Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

The burgeoning interest in synthesis and biological applications of 1,6-naphthyridines reflects the importance of 1,6-naphthyridines in the synthetic as well as medicinal chemistry fields. Specially, 1,6-naphthyridines are pharmacologically active, with variety of applications such as anticancer, anti-human immunodeficiency virus (HIV), anti-microbial, analgesic, anti-inflammatory and anti-oxidant activities. Although collective recent synthetic developments have paved a path to a wide range of functionalized 1,6-naphthyridines, a complete correlation of synthesis with biological activity remains elusive. The current review focuses on recent synthetic developments from the last decade and a thorough study of the anticancer activity of 1,6-naphthyridines on different cancer cell lines. Anticancer activity has been correlated to 1,6-naphthyridines using the literature on the structure–activity relationship (SAR) along with molecular modeling studies. Exceptionally, at the end of this review, the utility of 1,6-naphthyridines displaying activities other than anticancer has also been included as a glimmering extension.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
Scheme 44
Scheme 45
Scheme 46
Scheme 47
Scheme 48
Scheme 49
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Kumar D, Jain SK (2016) Curr Med Chem 23:4338–4394

    Article  CAS  PubMed  Google Scholar 

  2. Litvinov VP (2006) Adv Heterocycl Chem 91:189–300

    Article  CAS  Google Scholar 

  3. Garcia-Valverde M, Torroba T (2008) Molecules 10:318–320

    Article  Google Scholar 

  4. Zheng L, Bin Y, Wang Y, Hua R (2016) J Org Chem 81:8911–8919

    Article  CAS  PubMed  Google Scholar 

  5. Bracher F, Mink K (1995) Liebigs Ann 20:645–647

    Article  Google Scholar 

  6. Bennasar ML, Roca T, Zulaica E, Monerris M (2004) Tetrahedron 60:6785–6789

    Article  CAS  Google Scholar 

  7. Gross H, Goeger DE, Hills P, Mooberry SL, Ballantine DL, Murray TF, Valeriote FA, Gerwick WH (2006) J Nat Prod 69:640–644

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Zhang A, Ding C, Cheng C, Yao Q (2007) J Comb Chem 9:916–919

    Article  CAS  PubMed  Google Scholar 

  9. Kulakov IV, Shatsauskas AL, Matsukevich MV, Palamarchuk IV, Seilkhanov TM, Gatilov YV, Fisyuk AS (2017) Synthesis 49:3700–3709

    Article  CAS  Google Scholar 

  10. Okuma K, Oba A, Kuramoto R, Iwashita H (2017) Eur J Org Chem 2017:6885–6888

    Article  CAS  Google Scholar 

  11. Wang HY, Shi JJ, Wang C, Zhang XX, Wan Y, Wu H (2012a) Dye Pigment 95:268–274

    Article  CAS  Google Scholar 

  12. Patil SR, Shelar DP, Rote RV, Jachak MN (2011) J Fluoresc 21:2037–2052

    Article  CAS  PubMed  Google Scholar 

  13. Padhi SK, Tanaka K (2011) Inorg Chem 50:10718–10723

    Article  CAS  PubMed  Google Scholar 

  14. Noravyan AS, Paronikyan EG, Vartanyan SA (1986) Search New Drugs 85:439–448

    Google Scholar 

  15. Paudler WW, Kress TJ (1970) Adc Heterocycl Chem 11:123–175

    Article  CAS  Google Scholar 

  16. Paudler WW, Sheets RM (1983) Adc Heterocycl Chem 33:148–165

    Google Scholar 

  17. Hamada Y, Takeuchi I (2000) J Pharm Soc Jpn 120:206–223

    Article  CAS  Google Scholar 

  18. Ramhari VR, Sandeep MB, Deepak PS, Sandeep RP, Raghunath BT, Madhukar NJ (2011) J Heterocyclic Chem 48:301–307

    Article  Google Scholar 

  19. Madhukar NJ, Sandeep MB, Muddassar AK, Raghunath BT (2011) J Heterocyclic Chem 48:295–300

    Article  Google Scholar 

  20. Bodrin GV, Matveeva AG, Goryunov EI, Pasechnik MP, Aysin RR, Turanov AN, Karandashev VK, Savin ED, Peregudov AS, Nelyubina YV, Brel VK (2016) Chem Heterocycl Compd 52:583–591

    Article  CAS  Google Scholar 

  21. Hauser CR, Reynolds GA (1950) J Org Chem 15:1224–1232

    Article  CAS  Google Scholar 

  22. Manoj M, Prasad KJR (2012) Synth Commun 42:434–446

    Article  CAS  Google Scholar 

  23. Prabha K, Prasad KJR (2012) Synth Commun 42:2277–2289

    Article  CAS  Google Scholar 

  24. Varlamov AV, Guranova NI, Listratova AV, Borisova TN, Khrustalev VN, Titov AA, Voskressensky LG (2014) Chem Heterocycl Compd 50:264–270

    Article  CAS  Google Scholar 

  25. Rajanarendar E, Ramakrishna S, Kishore B (2014) J Heterocyclic Chem 51:1415–1420

    Article  CAS  Google Scholar 

  26. Dore A, Asproni B, Scampuddu A, Gessi S, Murineddu G, Cichero E, Fossa P, Merighi S, Bencivenni S, Pinna GA (2016) Bioorg Med Chem 24:5291–5301

    Article  CAS  PubMed  Google Scholar 

  27. Hassaneen HM, Wardkhan WW, Mohammed YS (2012) Heterocycles 85:2933–2947

    Article  CAS  Google Scholar 

  28. Vasilev LS, Surzhikov FE, Baranin SV, Dorokhov VA (2013) Russ Chem Bull Int Ed 62:1255–1261

    Article  CAS  Google Scholar 

  29. Hassaneen HM, Wardkhan WW, Mohammed YS (2013) Z Naturforsch 68b:895–904

    Article  Google Scholar 

  30. Khakwani S, Aslam S, Mussadiq S, Shahi MN, Perveen N, Benardino AMR, Khan MA (2016) Asian J Chem 28:2601–2604

    Article  CAS  Google Scholar 

  31. Prabha K (2016) Med Chem 6:62–71

    Article  Google Scholar 

  32. Ghotekar BK, Ghagare MG, Toche RB, Jachak MN (2010) Monatsh Chem 141:169–175

    Article  CAS  Google Scholar 

  33. Ravi M, Chauhan P, Singh S, Kant R, Yadav PP (2016) RSC Adv 6:48774–48778

    Article  CAS  Google Scholar 

  34. Selva Kumar AKMM, Rajkumar R, Rajendran SP (2015) Arch Appl Sci Res 7:60–64

    Google Scholar 

  35. Sarkar S, Das DK, Khan AT (2013) Eur J Org Chem 2013:6823–6830

    Article  CAS  Google Scholar 

  36. Verma AK, Jha RR, Chaudhary R, Tiwari RK, Reddy KSK, Danodia A (2012) J Org Chem 77:8191–8205

    Article  CAS  PubMed  Google Scholar 

  37. Hoplamaz E, Keskin S, Balci M (2017) Eur J Org Chem 2017:1489–1497

    Article  CAS  Google Scholar 

  38. Das P, Mukhopadhyay C (2014) Curr Microw Chem 1:98–109

    Article  CAS  Google Scholar 

  39. Mishra A, Rastogi N, Batra S (2012) Tetrahedron 68:2146–2154

    Article  CAS  Google Scholar 

  40. Sporar J, Bezensek J, Ursic U, Golobic A, Svete J, Stanovnik B (2011) Heterocycles 84:449–459

    Google Scholar 

  41. Moustafa MS, Al-Mousawi SM, Hilmy NM, Ibrahim YA, Liermann JC, Meier H, Elnagdi MH (2013) Molecule 18:276–286

    Article  CAS  Google Scholar 

  42. Abdel Hameed AM (2015) Environ Chem Lett 13:125–129

    Article  CAS  Google Scholar 

  43. Dotsenko VV, Ismiev AI, Khrustaleva AN, Frolov KA, Krivokolysko SG, Chigorina EA, Snizhko AP, Gromenko VM, Bushmarinov IS, Askerov RK, Pekhtereva TM, Suykov SY, Papayanina ES, Mazepa AV, Magerramov AM (2016) Chem Heterocycl Compd 52:473–483

    Article  CAS  Google Scholar 

  44. Suneel Kumar Y, Nawaz Khan F (2017a) Catal Lett 147:919–925

    Article  CAS  Google Scholar 

  45. Yu Y, Su R, Wang L, Qi W, He Z (2010) Med Chem Res 19:1233–1244

    Article  CAS  Google Scholar 

  46. Lukka PB, Paxton JW, Kestell P, Baguley BC (2012) Cancer Chemother Pharmacol 70:151–160

    Article  CAS  PubMed  Google Scholar 

  47. Feng W, Satyanarayana M, Cheng L, Liu A, Tsai YC, Liu LF, LaVoie EJ (2008) Bioorganic Med Chem 16:9295–9301

    CAS  Google Scholar 

  48. Feng W, Satyanarayana M, Tsai YC, Liu AA, Liu LF, LaVoie EJ (2009) Eur J Med Chem 44:3433–3438

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. Rudys S, Rios-Luci C, Perez-Roth E, Cikotiene I, Padron JM (2010) Bioorg Med Chem Lett 20:1504–1506

    Article  CAS  PubMed  Google Scholar 

  50. Kiselev E, Dexheimer TS, Pommier Y, Cushman M (2010) J Med Chem 53:8716–8726

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. Liu Q, Chang JW, Wang J, Kang SA, Thoreen CC, Markhard A, Hur W, Zhang J, Sim T, Sabatini DM, Gray NS (2010a) J Med Chem 53:7146–7155

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. Liu Q, Chang JW, Wang J, Kang SA, Thoreen CC, Markhard A, Hur W, Zhang J, Sim T, Sabatini DM, Gray NS (2010b) J Med Chem 2:7146–7155

    Article  Google Scholar 

  53. Lin S, Han F, Liu P, Tao J, Zhong X, Liu X, Yi C, Xu H (2014) Bioorg Med Chem Lett 24:790–793

    Article  CAS  PubMed  Google Scholar 

  54. Hunt JA, Kallashi F, Ruzek RD, Sinclair PJ, Ita I, McCormick SX, Pivnichny JV, Hop CECA, Kumar S, Wang Z, Keefe SJO, Neill EAO, Porter G, Thompson JE, Woods A, Zaller DM, Doherty JB (2003) Bioorg Med Chem Lett 13:467–470

    Article  CAS  PubMed  Google Scholar 

  55. Wang Y, Xu ZL, Ai J, Peng X, Lin JP, Ji YC, Geng MY, Long YQ (2013) Org Biomol Chem 11:1545–1562

    Article  CAS  PubMed  Google Scholar 

  56. Boezio AA, Copeland KW, Rex K, Albrecht BK, Bauer D, Bellon SF, Boezio C, Broome MA, Choquette D, Coxon A, Dussault I, Hirai S, Lewis R, Lin M-HJ, Lohman J, Liu J, Peterson EA, Potashman M, Shimanovich R, Teffera Y, Whittington DA, Vaida KR, Harmange JC (2016) J Med Chem 59:2328–2342

    Article  CAS  PubMed  Google Scholar 

  57. Elsayed MSA, Nielsen JJ, Park S, Park J, Liu Q, Kim CH, Pommier Y, Agama K, Low PS, Cushman M (2018) J Med Chem 61:10440–10462

    Article  CAS  PubMed  Google Scholar 

  58. Cywin CL, Zhao BP, McNeil DW, Hrapchak M, Prokopowicz AS, Goldberg DR, Morwick TM, Gao A, Jakes S, Kashem M, Magolda RL, Soll RM, Player MR, Bobko MA, Rinker J, DesJarlais RL, Winters MP (2003) Bioorg Med Chem Lett 13:1415–1418

    Article  CAS  PubMed  Google Scholar 

  59. Kaur M, Bahia MS, Silakari O (2012) J Chem Inf Model 52:2619–2630

    Article  CAS  PubMed  Google Scholar 

  60. Troiano V, Scarbaci K, Ettari R, Micale N, Cerchia C, Pinto A, Schirmeister T, Novellino E, Grasso S, Lavecchia A, Zappala M (2014) Eur J Med Chem 83:1–14

    Article  CAS  PubMed  Google Scholar 

  61. Bowling JJ, Pennaka HK, Ivey K, Wahyuono S, Kelly M, Schinazi RF, Valeriote FA, Graves DE, Hamann MT (2008) Chem Biol Drug Des 71:205–215

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. Kurtzberg LS, Roth S, Krumbholz R, Crawford J, Bormann C, Dunham S, Yao M, Rouleau C, Bagley RG, Yu XJ, Wang F, Schmid SM, LaVoie EJ, Teicher BA (2011) Clin Cancer Res 17:2777–2787

    Article  CAS  PubMed  Google Scholar 

  63. Barfacker L, Kuhl A, Hillisch A, Grosser R, Figueroa-Perez S, Heckroth H, Nitsche A, Erguden JK, Gielen-Haertwig H, Schlemmer KH, Mittendorf J, Paulsen H, Platzek J, Kolkhof P (2012) ChemMedChem 7:1385–1403

    Article  PubMed  Google Scholar 

  64. Mukhopadhyay C, Das P, Butcher RJ (2011) Org Lett 13:4664–4667

    Article  CAS  PubMed  Google Scholar 

  65. Nandi S, Islam MM, Saha M, Mitra S, Khatua S, Pal AK (2016) Synth Commun 46:1461–1476

    Article  CAS  Google Scholar 

  66. Das P, Chaudhuri T, Mukhopadhyay C, Comb ACS (2014) Sci 16:606–613

    CAS  Google Scholar 

  67. Li C, Mu XY, Li YL, Liu Y, Wang XS (2013) ACS Comb Sci 15:267–272

    Article  CAS  PubMed  Google Scholar 

  68. Okuma K, Koga T, Ozaki S, Suzuki Y, Horigami K, Nagahora N, Shioji K, Fukuda M, Deshimaru M (2014) Chem Commun 50:15525–15528

    Article  CAS  Google Scholar 

  69. Almansour AI, Kumar RS, Arumugam N, Basiri A, Kia Y, Ali MA (2015) Biomed Res Int 2015:1–9

    Article  Google Scholar 

  70. Dimmock JR, Padmanilayam MP, Puthucode RN, Nazarali AJ, Motaganahalli NL, Zello GA, Quail JW, Oloo EO, Kraatz HB, Prisciak JS, Allen TM, Santos CL, Balzarini J, Clercq ED, Manavathu EK (2001) J Med Chem 44(4):586–593

    Article  CAS  PubMed  Google Scholar 

  71. Lavanya M, Thirumalai D, Asharani IV, Aravindan PG (2015) RSC Adv 5:86330–86336

    Article  CAS  Google Scholar 

  72. Feng BB, Jin RZ, Zhang MM, Wang XS (2016) J Heterocyclic Chem 53:1578–1583

    Article  CAS  Google Scholar 

  73. Bin Feng B, Zhang MM, Wang XS (2016) Polycycl Aromat Compd 36:478–489

    Article  Google Scholar 

  74. Zhao Q, Yao CS, Wang XS (2018) Polycycl Aromat Compd 38:236–243

    Article  CAS  Google Scholar 

  75. Dandia A, Parewa V, Gupta SL, Sharma A, Rathore KS, Jain A (2015) Catal Commun 61:88–91

    Article  CAS  Google Scholar 

  76. Ray S, Das P, Banerjee B, Bhaumik A, Mukhopadhyay C (2015) ChemPlusChem 80:731–739

    Article  CAS  PubMed  Google Scholar 

  77. Wang HY, Shi JJ, Wang C, Zang XX, Wan Y, Wu H (2012) Dyes Pigm 95:268–274

    Article  CAS  Google Scholar 

  78. Feng GL, Ji SJ, Lai WY, Huang W (2006) Synlett 17:2841–2845

    Google Scholar 

  79. Singh RM, Kumar R, Sharma N, Asthana M (2013) Tetrahedron 69:9443–9450

    Article  CAS  Google Scholar 

  80. Singh JB, Chandra Bharadwaj K, Gupta T, Singh RM (2016) RSC Adv 6:26993–26999

    Article  CAS  Google Scholar 

  81. Kumar R, Asthana M, Singh RM (2017) J Org Chem 82:11531–11542

    Article  CAS  PubMed  Google Scholar 

  82. Suneel Kumar Y, Nawaz Khan FR (2017b) Chin Chem Lett 28:1607–1612

    Article  CAS  Google Scholar 

  83. Zeng LF, Wang Y, Kazemi R, Xu S, Xu ZL, Sanchez TW, Yang LM, Debnath B, Odde S, Xie H, Zheng Y-T, Ding J, Neamati N, Long Y-Q (2012) J Med Chem 55:9492–9509

    Article  CAS  PubMed  Google Scholar 

  84. Verma AK, Kotla SKR, Choudhary D, Patel M, Tiwari RK (2013) J Org Chem 78:4386–4401

    Article  CAS  PubMed  Google Scholar 

  85. Zahid M, Iaroshenko VO, Saghyan AS, Fischer C, Langer P (2013) Tetrahedron 69:3451–3458

    Article  CAS  Google Scholar 

  86. Mishra K, Singh JB, Gupta T, Singh RM (2017) Org Chem Front 4:1794–1798

    Article  CAS  Google Scholar 

  87. Muthukrishnan I, Vinoth P, Vivekanand T, Nagarajan S, Maheswari CU, Menendez JC, Sridharan V (2016) J Org Chem 81:1116–1124

    Article  CAS  PubMed  Google Scholar 

  88. Moustafa MS, Al-Mousawi SM, Elnagdi MH (2016) RSC Adv 6:90840–90845

    Article  CAS  Google Scholar 

  89. Sadek KU, Selim MA, Alnajjar A-A, Atallah M, Elnagdi MH (2016) Eur J Chem 7:468–472

    Article  CAS  Google Scholar 

  90. Al-Johani MA, Al-Zaydi KM, Mousally SM, Alqahtani NF, Elnagdi NH, Elnagdi MH (2017) Molecules 22:1–10

    Article  Google Scholar 

  91. Yang F, Zheng L, Xiang J, Dang Q, Bai X (2010) J Comb Chem 12:476–481

    Article  CAS  PubMed  Google Scholar 

  92. Zhang Y, Zhu Y, Zheng L, Zhuo LG, Yang F, Dang Q, Yu ZX, Bai X (2014) Eur J Org Chem 2014:660–669

    Google Scholar 

  93. Jouha J, Buttard F, Lorion M, Berthonneau C, Khouili M, Hiebel MA, Guillaumet G, Briere JF, Suzenet F (2017) Org Lett 19:4770–4773

    Article  CAS  PubMed  Google Scholar 

  94. Dong W, Yuan Y, Gao X, Hu B, Xie X, Zhang Z (2018) ChemCatChem 10:2878–2886

    Article  CAS  Google Scholar 

  95. Bagul SM, Birari DR, Ghagare MG, Toche RB, Jachak MN (2011) Monatsh Chem 142:169–175

    Article  CAS  Google Scholar 

  96. Glaisyer EL, Watt MS, Booker-Milburn KI (2018) Org Lett 20:5877–5880

    Article  CAS  PubMed  Google Scholar 

  97. Wang DL, Shi XC, Wang YY, Ma J (2016) Chin Chem Lett 27:261–264

    Article  CAS  Google Scholar 

  98. Tu MS, Li Y, Wang X, Jiang B, Wang SL, Tu SJ (2013) RSC Adv 3:3877–3880

    Article  CAS  Google Scholar 

  99. Abdelrazek FM, Metwally NH, Kassab NA, Sobhy NA, Metz P, Jaegerb A (2010) J Heterocyclic Chem 47:384–388

    CAS  Google Scholar 

  100. Asthana M, Sharma N, Singh RM (2014) Tetrahedron 70:7996–8003

    Article  CAS  Google Scholar 

  101. Ghoshal A, Yugandhar D, Nanubolu JB, Srivastava AK (2017) ACS Comb Sci 19:600–608

    Article  CAS  PubMed  Google Scholar 

  102. Metwally NH, Deeb EA (2018a) Synth Commun 48:1614–1628

    Article  CAS  Google Scholar 

  103. Han ZG, Miao CB, Shi F, Ning M, Zhang G, Tu SJ (2010) J Comb Chem 12:16–19

    Article  CAS  PubMed  Google Scholar 

  104. Buksnaitiene R, Cikotiene I (2012) Heterocycl Commun 18:87–92

    Article  CAS  Google Scholar 

  105. Bin Feng B, Lu L, Li C, Wang XS (2016) Org Biomol Chem 14:2774–2779

    Article  Google Scholar 

  106. Okada E, Hatakenaka M, Kuratani M, Mori T, Ashida T (2014) Heterocycles 88:799–806

    Article  CAS  Google Scholar 

  107. Muthukrishnan I, Vachan BS, Karuppasamy M, Eniyaval A, Uma Maheswari C, Nagarajan S, Menendez JC, Sridharan V (2019) Org Biomol Chem 17:6872–6879

    Article  CAS  PubMed  Google Scholar 

  108. Cailly T, Begtrup M (2010) Tetrahedron 66:1299–1307

    Article  CAS  Google Scholar 

  109. Agarwal PK, Saifuddin M, Kundu B (2010) Tetrahedron 66:862–870

    Article  CAS  Google Scholar 

  110. Meth-Cohn O, Narine B, Tarnowski B (1979) Tetrahedron Lett 20:3111–3114

    Article  Google Scholar 

  111. Patin A, Belmont P (2005) Synthesis 14:2400–2406

    Google Scholar 

  112. Sharma N, Asthana M, Nandini D, Singh RP, Singh RM (2013) Tetrahedron 69:1822–1829

    Article  CAS  Google Scholar 

  113. Wu JF, Liu MM, Huang SX, Wang Y (2015) Bioorg Med Chem Lett 25:3251–3255

    Article  CAS  PubMed  Google Scholar 

  114. Ramana PV, Prasad VK, Curie JR (2015) J Appl Chem 4:110–119

    CAS  Google Scholar 

  115. Bharath Kumar Reddy P, Ravi K, Mahesh K, Leelavathi P (2018) Tetrahedron Lett 59:4039–4043

    Article  CAS  Google Scholar 

  116. Wortmann L, Lindenthal B, Muhn P, Walter A, Nubbemeyer R, Heldmann D, Sobek L, Morandi F, Schrey AK, Moosmayer D, Gunther J, Kuhnke J, Koppitz M, Lucking U, Rohn U, Schafer M, Reppel KN, Kuhne R, Weinmann H, Langer G (2019) J Med Chem 62:10321–10341

    Article  CAS  PubMed  Google Scholar 

  117. Fiorito J, Vendome J, Saeed F, Staniszewski A, Zhang H, Yan S, Deng SX, Arancio O, Landry DW (2017) J Med Chem 60:8858–8875

    Article  CAS  PubMed  Google Scholar 

  118. Buttard F, Berthonneau C, Hiebel MA, Briere JF, Suzenet F (2019) J Org Chem 84:3702–3714

    Article  CAS  PubMed  Google Scholar 

  119. Peese KM, Allard CW, Connolly T, Johnson BL, Li C, Patel M, Sorensen ME, Walker MA, Meanwell NA, McAuliffe B, Minassian B, Krystal M, Parker DD, Lewis HA, Kish K, Zhang P, Nolte RT, Simmermacher J, Jenkins S, Cianci C, Narasimhulu Naidu B (2019) J Med Chem 62:1348–1361

    Article  CAS  PubMed  Google Scholar 

  120. Wang MS, Zhuo LS, Yang FP, Wang WJ, Huang W, Yang GF (2020) Eur J Med Chem 185:1–13

    Google Scholar 

  121. Ganggjee A, Ohemeng KA (1987) J Heterocyclic Chem 24:123–126

    Article  Google Scholar 

  122. Shen YC, Lin TT, Sheu JH, Duh CY (1999) J Nat Prod 62:1264–1267

    Article  CAS  PubMed  Google Scholar 

  123. Thompson AM, Connolly CJC, Hamby JM, Boushelle S, Hartl BG, Amar AM, Kraker AJ, Driscoll DL, Steinkampf RW, Patmore SJ, Vincent PW, Roberts BJ, Elliott WL, Klohs W, Leopold WR, Showalter HDH, Denny WA (2000) J Med Chem 43:4200–4211

    Article  CAS  PubMed  Google Scholar 

  124. Thompson AM, Rewcastle GW, Boushelle SL, Hartl BG, Kraker AJ, Lu GH, Batley BL, Panek RL, Hollis Showalter HD, Denny WA (2000) J Med Chem 43:3134–3147

    Article  CAS  PubMed  Google Scholar 

  125. Deady LW, Rodemann M, Zhuang L, Baguley BC, Denny WA (2003) J Med Chem 46:1049–1054

    Article  CAS  PubMed  Google Scholar 

  126. Deady LW, Rogers T, Zhuang L, Baguley BC, Denny WA (2005) Bioorg Med Chem 13:1341–1355

    Article  CAS  PubMed  Google Scholar 

  127. Deady LW, Rogers ML (2006) J Heterocyclic Chem 9:1–12

    Google Scholar 

  128. Ruchelman AL, Singh SK, Ray A, Wu XH, Yang JM, Li TK, Liu A, Liu LF, LaVoie EJ (2003) Bioorg Med Chem 11:2061–2073

    Article  CAS  PubMed  Google Scholar 

  129. Ruchelman AL, Kerrigan JE, Li TK, Zhou N, Liu A, Liu LF, LaVoie EJ (2004) Bioorg Med Chem 12:3731–3742

    Article  CAS  PubMed  Google Scholar 

  130. Ruchelman AL, Houghton PJ, Zhou N, Liu A, Liu LF, LaVoie EJ (2005) J Med Chem 48:792–804

    Article  CAS  PubMed  Google Scholar 

  131. Pettit GR, Hoffmann H, Herald DL, McNulty J, Murphy A, Higgs KC, Hamel E, Lewin NE, Pearce LV, Blumberg PM, Pettit RK, Knight JC (2004) J Org Chem 69:2251–2256

    Article  CAS  PubMed  Google Scholar 

  132. Pettit GR, Hoffmann H, McNulty J, Higgs KC, Murphy A, Molloy DJ, Herald DL, Williams MD, Pettit RK, Doubek DL, Hooper JNA, Albright L, Schmidt JM, Chapuis JC, Tackett LP (2004) J Nat Prod 67:506–509

    Article  CAS  PubMed  Google Scholar 

  133. Pettit GR, Hoffmann H, Herald DL, Blumberg PM, Hamel E, Schmidt JM, Chang Y, Pettit RK, Lewin NE, Pearce LV (2004) J Med Chem 47:1775–1782

    Article  CAS  PubMed  Google Scholar 

  134. Zhou Y, Beeler AB, Cho S, Wang Y, Franzblau SG, Snyder JK (2008) J Comb Chem 10:534–540

    Article  CAS  PubMed  Google Scholar 

  135. Bridewell DJA, Porter ACG, Finlay GJ, Baguley BC (2008) Cancer Chemother Pharmacol 62:753–762

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  136. Li Y, Liang J, Siu T, Hu E, Rossi MA, Barnett SF, Defeo-Jones D, Jones RE, Robinson RG, Leander K, Huber HE, Mittal S, Cosford N, Prasit P (2009) Bioorg Med Chem Lett 19:834–836

    Article  CAS  PubMed  Google Scholar 

  137. Sharma L, Tsai YC, Liu AA, Liu LF, LaVoie EJ (2009) Eur J Med Chem 44:1471–1476

    Article  CAS  PubMed  Google Scholar 

  138. Chen YY, Finlay GJ, Kirker JA, Marshall ES, Richardson E, Baguley BC (2011) Invest New Drugs 29:1504–1510

    Article  CAS  PubMed  Google Scholar 

  139. Desbois N, Pertuit D, Moretto J, Cachia C, Chauffert B, Bouyer F (2013) Eur J Med Chem 69:719–727

    Article  CAS  PubMed  Google Scholar 

  140. Insuasty B, Becerra D, Quiroga J, Abonia R, Nogueras M, Cobo J (2013) Eur J Med Chem 60:1–9

    Article  CAS  PubMed  Google Scholar 

  141. Prabha K, Prasad KJR (2013) Med Chem Comm 4:340–346

    Article  CAS  Google Scholar 

  142. Dyshlovoy SA, Fedorov SN, Shubina LK, Kuzmich AS, Bokemeyer C, Keller-Von Amsberg G, Honecker F (2014) Biomed Res Int 2014:1–7

    Article  Google Scholar 

  143. Murugesh AAM, Selvakumar M, Rajendran SP (2014) Int J Appl Biol Pharm 5:85–89

    Google Scholar 

  144. Mallinger A, Schiemann K, Rink C, Sejberg J, Honey MA, Czodrowski P, Stubbs M, Poeschke O, Busch M, Schneider R, Schwarz D, Musil D, Burke R, Urbahns K, Workman P, Wienke D, Clarke PA, Raynaud FI, Eccles SA, Esdar C, Rohdich F, Blagg J, Med ACS (2016) Chem Lett 7:573–578

    CAS  Google Scholar 

  145. Montoir D, Barille-Nion S, Tonnerre A, Juin P, Duflos M, Bazin MA (2016) Eur J Med Chem 119:17–33

    Article  CAS  PubMed  Google Scholar 

  146. Frasson I, Spano V, Di Martino S, Nadai M, Doria F, Parrino B, Carbone A, Cascioferro SM, Diana P, Cirrincione G, Freccero M, Barraja P, Richter SN, Montalbano A (2019) Eur J Med Chem 162:176–193

    Article  CAS  PubMed  Google Scholar 

  147. Xu G, Gao Y, Sun B, Peng L, Mao L, Jiang Y, Ding Q (2018) J Heterocycl Chem 55:2151–2156

    Article  CAS  Google Scholar 

  148. Metwally NH, Deeb EA (2018b) Bioorg Chem 77:203–214

    Article  CAS  PubMed  Google Scholar 

  149. Liu C, Tang X, Li P, Li G (2012) Org Lett 14:1994–1997

    Article  CAS  PubMed  Google Scholar 

  150. Kallmeyer ST, Rubin JR, Humblet C, Hamby JM, Showalter HDH (1998) J Med Chem 41:1752–1763

    Article  Google Scholar 

  151. Cushman M, Jayaraman M, Vroman JA, Fukunaga AK, Fox BM, Kohlhagen G, Strumberg D, Pommier Y (2000) J Med Chem 43:3688–3698

    Article  CAS  PubMed  Google Scholar 

  152. Utkina NK, Chaikina EL, Anisimov MM (2017) Nat Prod Commun 12:1437–1438

    Google Scholar 

  153. Pagar BP (2019) Asian J Chem 31:79–82

    Article  CAS  Google Scholar 

  154. Khakwani S, Aslam S, Shahi MN, Mussadiq S, Benardino AMR, Khan MA (2017) Asian J Chem 29:27–30

    Article  CAS  Google Scholar 

  155. Suresh T, Dhanabal T, Kumar RN, Mohan PS (2005) Ind J Chem 44B:2375–2379

    CAS  Google Scholar 

  156. Wadood FKA, Monem MIA, Fahmy AM, Geies AA (2008) Z Naturforsch 63:303–312

    Article  Google Scholar 

  157. Sabatini S, Cecchetti V, Tabarrini O, Fravolini A (1999) J Heterocyclic Chem 36:953–957

    Article  CAS  Google Scholar 

  158. Sanchez JP, Gogliotti RD (1993) J Heterocyclic Chem 30:855–859

    Article  CAS  Google Scholar 

  159. Chan L, Jin H, Stefanac T, Lavallee JF, Falardeau G, Wang W, Bedard J, May S, Yuen L (1999) J Med Chem 42:3023–3025

    Article  CAS  PubMed  Google Scholar 

  160. Elslager EF, Tendick FH, Vi SA, Elslager EF, Tendick FH, Arbor A (1961) J Org Chem 5:546–558

    Google Scholar 

  161. Borne RF, Kim Fifer E, Waters IW (1984) J Med Chem 27:1271–1275

    Article  CAS  PubMed  Google Scholar 

  162. Vatsadze SZ, Kostochka ML, Lezina VP, Vinokurov VG, Klodt PM, Zyk NV (2005) Russ Chem Bull Int Ed 54:257–258

    Article  CAS  Google Scholar 

  163. Makarem MS, Nasser AH, Mamdouh MA, Hanem MA, Megeid A, Farouk ME (2014) Der Pharma Chemica 6:394–410

    Google Scholar 

  164. Hinschberger A, Butt S, Lelong V, Boulouard M, Dumuis A, Dauphin F, Bureau R, Pfeiffer B, Renard P, Rault S (2003) J Med Chem 46:138–147

    Article  CAS  PubMed  Google Scholar 

  165. Sylvain R, Antoine H, Francois D, Michel B, Aline D (2001) WO 2001079205 A1 20011025

  166. Thompson AM, Delaney AM, Hamby JM, Schroeder MC, Spoon TA, Crean SM, Showalter HDH, Denny WA (2005) J Med Chem 48:4628–4653

    Article  CAS  PubMed  Google Scholar 

  167. Wortmann L, Lindenthal B, Muhn P, Walter A, Nubbemeyer R, Heldmann D, Sobek L, Morandi F, Schrey AK, Moosmayer D, Gunther (2019) J Med Chem 62:10321–10341

    Article  CAS  PubMed  Google Scholar 

  168. Zhuang L, Wai JS, Embrey MW, Fisher TE, Egbertson MS, Payne LS, Guare JP, Vacca JP, Hazuda DJ, Felock PJ, Wolfe AL, Stillmock KA, Witmer MV, Moyer G, Schleif WA, Gabryelski LJ, Leonard YM, Lynch JJ, Michelson SR, Young SD (2003) J Med Chem 46:453–456

    Article  CAS  PubMed  Google Scholar 

  169. Peese KM, Allard CW, Connolly T, Johnson BL, Li C, Patel M, Sorensen ME, Walker MA, Meanwell NA, McAuliffe B, Minassian B (2019) J Med Chem 62:1348–1361

    Article  CAS  PubMed  Google Scholar 

  170. Clark RD, Repke DB, Berger J, Nelson JT, Kilpatrick AT, Brown CM, MacKinnon AC, Clague RU, Spedding M (1991) J Med Chem 34:705–717

    Article  CAS  PubMed  Google Scholar 

  171. Falardeau G, Lachance H, St-Pierre A, Yannopoulos CG, Drouin M, Bedard J, Chan L (2005) Bioorg Med Chem Lett 15:1693–1695

    Article  CAS  PubMed  Google Scholar 

  172. Bernardino A, Azevedo AR, Pinheiro LCS, Borges JC, Paixao ICP, Mesquita M, Souza TML, Dos Santos MS (2012) Org Med Chem Lett 2(3):1–7

    Google Scholar 

  173. Bernardino AM, Castro HC, Frugulhetti IC, Loureiro NI, Azevedo AR, Pinheiro LC, Souza TM, Giongo V, Passamani F, Magalhaes UO, Albuquerque MG (2008) Bioorg Med Chem 16:313–321

    Article  CAS  PubMed  Google Scholar 

  174. Gorecki DKJ, Hawes EM (1977) J Med Chem 20:124–128

    Article  CAS  Google Scholar 

  175. Hawes EM, Gorecki DK, Johnson DD (1973) J Med Chem 16:849–853

    Article  CAS  PubMed  Google Scholar 

  176. Di Pietro O, Viayna E, Vicente-Garcia E, Bartolini M, Ramon R, Juarez-Jimenez J, Clos MV, Perez B, Andrisano V, Luque FJ, Lavilla R, Torrero DM (2014) Eur J Med Chem 73:141–152

    Article  PubMed  Google Scholar 

  177. Vanlaer S, Voet A, Gielens C, De Maeyer M, Compernolle F (2009) Eur J Org Chem 20:643–654

    Article  Google Scholar 

  178. Di Pietro O, Perez-Areales FJ, Juarez-Jimenez J, Espargaro A, Clos MV, Perez B, Lavilla R, Sabate R, Luque FJ, Munoz-Torrero D (2014) Eur J Med Chem 84:107–117

    Article  PubMed  Google Scholar 

  179. Austin NE, Hadley MS, Harling JD, Harrington FP, Macdonald GJ, Mitchell DJ, Riley GJ, Stean TO, Stemp G, Stratton SC, Thompson M (2003) Bioorg Med Chem Lett 13:1627–1629

    Article  CAS  PubMed  Google Scholar 

  180. Cruz D, Wang Z, Kibbie J, Modlin R, Kwon O (2011) Proc Natl Acad Sci USA 108:6769–6774

    Article  CAS  PubMed  Google Scholar 

  181. Singh B, Bacon ER, Lesher GY, Robinson S, Pennock PO, Bode DC, Pagani ED, Bentley RG, Connell MJ, Hamel LT, Silver PJ (1995) J Med Chem 38:2546–2550

    Article  CAS  PubMed  Google Scholar 

  182. Wang HY, Shi JJ, Wang C, Zhang XX, Wan Y, Wu H (2012b) Dyes Pigm 95:268–274

    Article  CAS  Google Scholar 

  183. Wang H, Shi J, Wang X, Zhang X, Zhao L, Wan Y, Wu H (2013) Spectrochem Acta A Mol Biomol Spect 103:62–67

    Article  CAS  Google Scholar 

  184. Bauer U, Giordanetto F, Bauer M, Mahony GO, Johansson KE, Knecht W, Hartleib-Geschwindner J, Carlsson ET, Enroth C (2012) Bioorg Med Chem Lett 22:1944–1948

    Article  CAS  PubMed  Google Scholar 

  185. Sun B, Chen J, Ye F, Lu Y, Xu G, Mao L, Gao Y, Zhang H, Wang H, Peng L (2019) ChemistrySelect 4:6552–6556

    Article  CAS  Google Scholar 

  186. Li H, Sun W, Huang X, Lu X, Patel PR, Kim M, Orr MJ, Fisher RM, Tanaka TQ, Mckew JC, Simeonov A, Sanderson PE, Zheng W, Williamson KC, Huang W (2017) ACS Comb Sci 19:748–754

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge Sichuan Youth Science and Technology Foundation (Grant no. 2017JQ0010); Explorative Project (Grant no. G201601) of State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation from Southwest Petroleum University; National High Technology Research and Development Program (Grant nos. 2016ZX05053 and 2016ZX05014-005-007); Key endowment Project of Educational Commission of Sichuan Province (Grant no. 16CZ0008) and China Postdoctoral Science Foundation (2019M650250), and the National Natural Science Foundation of China (Grant no. 41902303) for their support.

Author information

Authors and Affiliations

  1. State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu, 610500, Xindu, People’s Republic of China

    Mallu Lavanya, Chong Lin, Jincheng Mao, Sreenath Reddy Aabaka, Xiaojiang Yang, Jinhua Mao & Jinzhou Zhao

  2. School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu, 610500, People’s Republic of China

    Mallu Lavanya & Zhiyu Huang

  3. Department of Chemistry, Thiruvalluvar University, Vellore, 632 115, Tamil Nadu, India

    Dhakshanamurthy Thirumalai

Authors
  1. Mallu Lavanya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chong Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jincheng Mao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dhakshanamurthy Thirumalai
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sreenath Reddy Aabaka
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xiaojiang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jinhua Mao
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Zhiyu Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Jinzhou Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Chong Lin, Jincheng Mao or Dhakshanamurthy Thirumalai.

Ethics declarations

Conflict of interest

There are no conflicts to declare.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lavanya, M., Lin, C., Mao, J. et al. Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines. Top Curr Chem (Z) 379, 13 (2021). https://doi.org/10.1007/s41061-020-00314-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-020-00314-6

Keywords

Search

Navigation