Skip to main content

Advertisement

SpringerLink
Log in

Convenient synthesis, anticancer evaluation and QSAR studies of some thiazole tethered indenopyrazoles

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

A convenient one-pot synthesis of twelve new thiazole tethered indeno[1,2-c]pyrazol-4-ones (3a–3l) was carried out by three-component reaction between 1,3-diketones, thiosemicarbazide and α-bromoketones in high yields. Wolff-Kishner reduction of indeno[1,2-c]pyrazol-4-ones (3a–3l) led to the formation of corresponding indeno[1,2-c]pyrazoles (4a–4l) in moderate-to-good yields. The structures of all the synthesized indenopyrazoles were elucidated by IR, 1H NMR, 13C NMR and mass spectral techniques. In vitro cytotoxicity of thiazole tethered indenopyrazoles (3a–3l & 4a–4l) was evaluated against different human cancer cell lines, viz. human renal carcinoma (A498), human colorectal adenocarcinoma (HT29), human breast adenocarcinoma (MCF-7), human hepatocellular carcinoma (HepG2) and normal cell line, i.e., normal rat kidney epithelial (NRK). Among all the tested derivatives, 4a, 4d and 4h exhibited better activity against HT29 cancer cell line. The statistically significant QSAR models were developed for all the cancer cell lines using multiple linear regression analysis to understand the observed activity trend on structural basis.

Graphical Abstract

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  • Abdou MI, Saleh AM, Zohdi HF (2004) Synthesis and antitumor activity of 5-trifluoromethyl-2,4-dihydropyrazol-3-one nucleosides. Molecules 9:109–116

    Article  CAS  PubMed  Google Scholar 

  • Agrawal VK, Sharma R, Khadikar PV (2002) QSAR studies on antimalarial substituted phenyl analogues and their Nω-Oxides. Bioorg Med Chem 10:1361–1366

    Article  CAS  PubMed  Google Scholar 

  • Ahsan MJ, Samy JG, Soni S, Jain N, Kumar L, Sharma LK, Yadav H, Saini L, Kalyansing RG, Devenda NS, Prasad R, Jain CB (2011) Discovery of novel antitubercular 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues. Bioorg Med Chem Lett 21:5259–5261

    Article  CAS  PubMed  Google Scholar 

  • Altıntop MD, Ozdemir A, Ilgın S, Atli O (2014) Synthesis and biological evaluation of new pyrazole-based thiazolyl hydrazone derivatives as potential anticancer agents. Lett Drug Des Discov 11:833–839

    Article  Google Scholar 

  • Andreani A, Rambaldi M, Mascellani G, Rugarli P (1987) Synthesis and diuretic activity of imidazo[2,1-b]thiazole acetohydrazones. Eur J Med Chem 22:19–22

    Article  CAS  Google Scholar 

  • Arshad MF, Siddiqui N, Elkerdasy A, Alrohaimi AH, Khan SA (2014) Anticonvulsant and neurotoxicity evaluation of some newly synthesized thiazolyl coumarin derivatives. Am J Pharmacol Toxicol 9:132–138

    Article  Google Scholar 

  • Baumann K, Stiefl N (2004) Validation tools for variable subset regression. J Comput-Aided Mol Des 18:549–562

    Article  CAS  PubMed  Google Scholar 

  • Bekhit AA, Ashour HMA, Ghany YSA, Bekhit AEA, Baraka A (2008) Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Eur J Med Chem 43:456–463

    Article  CAS  PubMed  Google Scholar 

  • Bhosale PP, Chavan RS, Bhosale AV (2012) Design, synthesis, biological evaluation of thiazolyl Schiff base derivatives as novel anti-inflammatory agents. Indian J Chem, Sect B 51:1649–1654

    Google Scholar 

  • Chong WKM, Duvadie RK (2003) Pyrazole-thiazole compounds, pharmaceutical compositions containing them. US Patent 6566363 B2, Filed Aug 8, 2001, Issued May 20, 2003

  • Dawood KM, Eldebss TMA, El-Zahabi HAS, Yousef MH, Metz P (2013) Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents. Eur J Med Chem 70:740–749

    Article  CAS  PubMed  Google Scholar 

  • Denizot F, Lang R (1986) Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 89:271–277

    Article  CAS  PubMed  Google Scholar 

  • Deverakonda M, Doonaboina R, Vanga S, Vemu J, Boni S, Mailavaram RP (2013) Synthesis of novel 2-alkyl-4-substituted-amino-pyrazolo[3,4-d]pyrimidines as new leads for anti-bacterial and anti-cancer activity. Med Chem Res 22:1090–1101

    Article  Google Scholar 

  • Dhawan SN, Dasgupta S, Mor S, Gupta SC (1993) Orientational preferences in the synthesis of some indeno[2,1-c]quinolin-7(H)-ones. Indian J Heterocycl Chem 2:155–158

    CAS  Google Scholar 

  • Dhawan SN, Mor S, Sharma K, Chawla AD, Saini A, Gupta SC (1994) On the mechanism of formation of pyrazoles from 1,3-diketones and hydrazines: isolation of hydroxypyrazoline intermediates. Indian J Chem, Sect B 33:38–42

    Google Scholar 

  • Elguero J, Goya P, Jagerovic N, Silva AMS (2002) Pyrazoles as drugs: facts and fantasies. In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems, vol 6. Royal Society of Chemistry, Cambridge, pp 52–98

    Google Scholar 

  • Farghaly AA, Bekhit AA, Park JY (2000) Design and synthesis of some oxadiazolyl, thiadiazolyl, thiazolidinyl, and thiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Arch Pharm Pharm Med Chem 333:53–57

    Article  CAS  Google Scholar 

  • Flores MC, Loev B (1961) Process for preparing pyrazoloindenone hydrazones. US Patent 2,989,538, June 20, 1961

  • Furusjo E, Svenson A, Rahmberg M, Andersson M (2006) The importance of outlier detection and training set selection for reliable environmental QSAR predictions. Chemosphere 63(1):99–108

    Article  PubMed  Google Scholar 

  • Gaikwad ND, Patil SV, Bobade VD (2013) Synthesis and antimicrobial activity of novel thiazole substituted pyrazole derivatives. J Hetrocycl Chem 50:519–527

    Article  CAS  Google Scholar 

  • Golbraikh A, Tropsha A (2002) Beware of q2! J Mol Graph Model 20:269–276

    Article  CAS  PubMed  Google Scholar 

  • Gramatica P (2007) Principles of QSAR models validation: internal and external. QSAR Comb Sci 26:694–701

    Article  CAS  Google Scholar 

  • Gu L, Jin C (2012) Synthesis and antitumor activity of α-aminophosphonates containing thiazolo[5,4-b]pyridine moiety. Org Biomol Chem 10:7098–7102

    Article  CAS  PubMed  Google Scholar 

  • Gupta SC, Quarishi MA, Dhawan SN (1979) Synthesis of 6-phenyl-7H-indeno[2,1-c]quinoline & 2-methyl-6-phenyl-7H-indeno[2,1-c]quinoline. Indian J Chem, Sect B 18:547–548

    Google Scholar 

  • Hall LH, Kier LB (1995) Electrotopological state indices for atom types: a novel combination of electronic, topological, and valence state information. J Chem Inf Comput Sci 35:1039–1045

    Article  CAS  Google Scholar 

  • Hamilton RW (1976) The antiarrhythmic and anti-inflammatory activity of a series of tricyclic pyrazoles. J Heterocycl Chem 13:545–553

    Article  CAS  Google Scholar 

  • Hargrave KD, Hess FK, Oliver JT (1983) N-(4-substituted thiazolyl)oxamic acid derivatives, new series of potent, orally active antiallergy agents. J Med Chem 26:1158–1163

    Article  CAS  PubMed  Google Scholar 

  • Hughes DW, Nalliah BC, Holland HL, Maclean DB (1977) 13C nuclear magnetic resonance spectra of the spirobenzylisoquinoline alkaloids and related model compounds. Can J Chem 55:3304–3311

    Article  CAS  Google Scholar 

  • Karale BK, Takate SJ, Salve SP, Zaware BH, Jadhav SS (2015) Synthesis and biological screening of some novel thiazolyl chromones and pyrazoles. Indian J Chem, Sect B 54:798–804

    Google Scholar 

  • Kartalou M, Essigmann JM (2001) Mechanisms of resistance to cisplatin. Mutation Res 478:23–43

    Article  CAS  PubMed  Google Scholar 

  • Kim KS, Kimball SD, Misra RN, Rawlins DB, Hunt JT, Xiao HY, Lu S, Qian L, Han WC, Shan W, Mitt T, Cai ZW, Poss MA, Zhu H, Sack JS, Tokarski JS, Chang CY, Pavletich N, Kamath A, Humphreys WG, Marathe P, Bursuker I, Kellar KA, Roongta U, Batorsky R, Mulheron JG, Bol D, Fairchild CR, Lee FY, Webster KR (2002) Discovery of aminothiazole inhibitors of cyclin-dependent kinase 2: synthesis, X-ray crystallographic analysis, and biological activities. J Med Chem 45:3905–3927

    Article  CAS  PubMed  Google Scholar 

  • Lapenna S, Giordano A (2009) Cell cycle kinases as therapeutic targets for cancer. Nat Rev Drug Discov 8:547–566

    Article  CAS  PubMed  Google Scholar 

  • Lemke TL, Sawhney KN (1982) The regiospecific synthesis of N-substituted pyrazoles. I. 1- and 2-substituted indeno[1,2-c]pyrazol-4(1H)-ones. J Heterocycl Chem 19:1335–1340

    Article  CAS  Google Scholar 

  • Lemke TL, Cramer MB, Shanmugam K (1978) Heterocyclic tricycles as potential CNS agents I: 4-aminoalkylindeno[1,2-c]pyrazoles. J Pharma Sci 67:1377–1381

    Article  CAS  Google Scholar 

  • Lemke TL, Abebe E, Moore PF, Carty TJ (1989) Indeno[1,2-c]pyrazolone acetic acids as semirigid analogues of the nonsteroidal anti-inflammatory drugs. J Pharma Sci 78:343–347

    Article  CAS  Google Scholar 

  • Liu S, Cao C, Li Z (1998) Approach to estimation and prediction for normal boiling point (NBP) of alkanes based on a novel molecular distance edge (MDE) Vector, Lambda. J Chem Inf Comput Sci 38:387–394

    Article  CAS  Google Scholar 

  • Loev B, Mosher WA (1961) Pyrazoloindenone azines. US Patent 2,969,374, Jan 24, 1961

  • Long W, Xiang J, Wu H, Hu W, Zhang X, Jin J, He X, Shen X, Zhou Z, Fan S (2013) QSAR modeling of iNOS inhibitors based on a novel regression method: multi-stage adaptive regression. Chemom Intell Lab Syst 128:83–88

    Article  CAS  Google Scholar 

  • Maggio B, Raffa D, Raidmondi MV, Cusimano MG, Plescia F, Cascioferro S, Cancemi G, Lauricella M, Carlisi D, Daidone G (2014) Synthesis and antiproliferative activity of new derivatives containing the polycyclic system 5,7:7,13-dimethanopyrazolo[3,4-b]pyrazolo[3′,4′:2,3]azepino[4,5-f]azocine. Eur J Med Chem 72:1–9

    Article  CAS  PubMed  Google Scholar 

  • Minegishi H, Fukashiro S, Ban HS, Nakamura H (2013) Discovery of indenopyrazoles as a new class of Hypoxia Inducible Factor (HIF)-1 inhibitors. ACS Med Chem Lett 4:297–301

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Misra RN, Xiao HY, Kim KS, Lu S, Han WC, Barbosa SA, Hunt JT, Rawlins DB, Shan W, Ahmed SZ, Qian L, Chen BC, Zhao R, Bednarz MS, Kellar KA, Mulheron JG, Batorsky R, Roongta U, Kamath A, Marathe P, Ranadive SA, Sack JS, Tokarski JS, Pavletich NP, Lee FYF, Webster KR, Kimball SD (2004) N-(Cycloalkylamino)acyl-2-aminothiazole inhibitors of cyclin-dependent kinase 2. N-[5-[[[5-(1,1-Dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide (BMS-387032), a highly efficacious and selective antitumor agent. J Med Chem 47:1719–1728

    Article  CAS  PubMed  Google Scholar 

  • Mohil R, Kumar D, Mor S (2014) Synthesis and antimicrobial activity of some 1,3-disubstituted indeno[1,2-c]pyrazoles. J Heterocycl Chem 51:203–211

    Article  CAS  Google Scholar 

  • Mor S, Mohil R, Kumar D, Ahuja M (2012a) Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles. Med Chem Res 21:3541–3548

    Article  CAS  Google Scholar 

  • Mor S, Pahal P, Narasimhan B (2012b) Synthesis, characterization, antimicrobial activities and QSAR studies of some 10a-phenylbenzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones. Eur J Med Chem 53:176–189

    Article  CAS  PubMed  Google Scholar 

  • Mor S, Pahal P, Narasimhan B (2012c) Synthesis, characterization, biological evaluation and QSAR studies of 11-p-substituted phenyl-12-phenyl-11a,12-dihydro-11H-indeno[2,1-c][1,5]benzothiazepines as potential antimicrobial agents. Eur J Med Chem 57:196–210

    Article  CAS  PubMed  Google Scholar 

  • Mosher WA, Soeder RW (1971) 3-Cycloalkyl- and 3-heterocyclic substituted indeno[1,2-c]pyrazol-4(1H)ones. J Heterocycl Chem 8:855–859

    Article  CAS  Google Scholar 

  • Nugiel DA, Vidwans A, Etzkorn AM, Rossi KA, Benfield PA, Burton CR, Cox S, Doleniak D, Seitz SP (2002) Synthesis and evaluation of indenopyrazoles as cyclin-dependent kinase inhibitors. 2. Probing the indeno ring substituent pattern. J Med Chem 45:5224–5232

    Article  CAS  PubMed  Google Scholar 

  • Pandya KS, Khan N (2008) Synthesis and antimicrobial study of novel 1-aryl-2-oxo-indano[3,2-d]pyrido/pyrimido[1,2-b]pyrimidines. Arch Pharm Chem Life Sci 341:418–423

    Article  Google Scholar 

  • Patra A, Mishra SK (1991) Carbon-13 NMR signals of some substituted indanones, tetralones and benzo-α-pyrones, β-substituted β-phenylpropionic acids and related compounds. Magn Reson Chem 29:749–752

    Article  CAS  Google Scholar 

  • Patt WC, Hamilton HW, Taylor MD, Ryan MJ, Taylor DG Jr, Connolly CJC, Doherty AM, Klutchko SR, Sircar I, Steinbaugh BA, Batley BL, Painchaud CA, Rapundalo ST, Michniewicz BM, Olson SCJ (1992) Structur-activity relationships of a series of 2-amino-4-thiazole containing rennin inhibitors. J Med Chem 35:2562–2572

    Article  CAS  PubMed  Google Scholar 

  • Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC (1997) Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib). J Med Chem 40:1347–1365

    Article  CAS  PubMed  Google Scholar 

  • Pignatello R, Mazzone S, Panico AM, Mazzone G, Penissi G, Castana R, Matera M, Blandino G (1991) Synthesis and biological evaluation of thiazolo-triazole derivatives. Eur J Med Chem 26:929–938

    Article  CAS  Google Scholar 

  • Rabik CA, Dolan ME (2007) Molecular mechanisms of resistance and toxicity associated with platinating agents. Cancer Treatment Rev 33:9–23

    Article  CAS  Google Scholar 

  • Rawal RK, Tripathi R, Katti SB, Pannecouque C, Clercq ED (2008) Design and synthesis of 2-(2,6-dibromophenyl)-3-heteroaryl-1,3-thiazolin-4-ones as anti-HIV agents. Eur J Med Chem 43:2800–2806

    Article  CAS  PubMed  Google Scholar 

  • Rostom SAF (2006) Synthesis and in vitro antitumor evaluation of some indeno[1,2-c]-pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores, and some derived thiazole ring systems. Bioorg Med Chem 14:6475–6485

    Article  CAS  PubMed  Google Scholar 

  • Roy K, Das RN (2011) On some novel extended topochemical atom (ETA) parameters for effective encoding of chemical information and modeling of fundamental physicochemical properties. SAR QSAR Environ Res 22:451–472

    Article  CAS  PubMed  Google Scholar 

  • Roy K, Ghosh G (2004) QSTR with extended topochemical atom indices. 2. Fish toxicity of substituted benzenes. J Chem Inf Comput Sci 44:559–567

    Article  CAS  PubMed  Google Scholar 

  • Samadhiya P, Sharma R, Srivastava SK (2013) Synthesis and antitubercular activity of 4-oxo-thiazolidine derivatives of 2-amino-5-nitrothiazole. Bull Chem Soc Ethiop 27:249–263

    Google Scholar 

  • Shapiro L, Geiger K, Freedman L (1960) Indandione anticoagulants. J Org Chem 25:1860–1865

    Article  CAS  Google Scholar 

  • Shi LM, Fang H, Tong W, Wu J, Perkins R, Blair RM, Branham WS, Dial SL, Moland CL, Sheehan DM (2001) QSAR models using a large diverse set of estrogens. J Chem Inf Comput Sci 41:186–195

    Article  CAS  PubMed  Google Scholar 

  • Shih MH, Su YS, Wu CL (2007) Syntheses of aromatic substituted hydrazine-thiazole derivatives to clarify structural characterization and antioxidant activity between 3-arylsydnonyl and aryl substituted hydrazine-thiazoles. Chem Pharm Bull 55:1126–1135

    Article  CAS  PubMed  Google Scholar 

  • Sigroha S, Narasimhan B, Kumar P, Khatkar A, Ramasamy K, Mani V, Mishra RK, Majeed ABA (2012) Design, synthesis, antimicrobial, anticancer evaluation and QSAR studies of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones. Med Chem Res 21:3863–3875

    Article  CAS  Google Scholar 

  • Singh SP, Sehgal S, Tarar LS (1989) Synthesis & NMR spectra of 2-(pyrazol-1yl)benzothiazoles: unambiguous assignment of 3- & 5-substituents of pyrazole moiety. Indian J Chem B 28:27–31

    Google Scholar 

  • Song YL, Yang T, Dong YF, Wu F, Yang GL (2014) Facile one-pot synthesis of some thiazolyl-pyrazole derivatives with antifungal activity. Chem Lett 43:134–136

    Article  CAS  Google Scholar 

  • Suresh N (2013) Human androgen receptor inhibitors: computational 3D QSAR studies to design lead compounds for treatment of prostate cancer. Turk J Biochem 38:262–269

    Article  CAS  Google Scholar 

  • Tao Z, Sowin TJ, Lin N (2005) A facile synthesis of antitumoral indeno[1,2-c]pyrazole-4-one by mild oxidation with molecular oxygen. Tetrahedron Lett 46:7615–7618

    Article  CAS  Google Scholar 

  • Tao Z, Li G, Tong Y, Stewart KD, Chen Z, Bui M, Merta P, Park C, Kover P, Zhang H, Sham HL, Rosenberg SH, Sowin TJ, Lin N (2007) Discovery of 4′-(1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-benzonitriles and 4′-(1,4-diydro-indeno[1,2-c]pyrazol-3-yl)-pyridine-2′-carbonitriles as potent checkpoint kinase 1 (Chk1) inhibitors. Bioorg Med Chem Lett 17:5944–5951

    Article  CAS  PubMed  Google Scholar 

  • Terrett NK, Bell AS, Brown D, Ellis P (1996) (VIAGRA™), a potent and selective inhibitor of type 5cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg Med Chem Lett 6:1819–1824

    Article  Google Scholar 

  • Thakar AS, Singh KK, Joshi KT, Pancholi AM, Pandya KS (2010) Synthesis, characterization and antibacterial activity of Schiff bases and their metal complexes derived from 4-acyl-1-phenyl-3-methyl-2-pyrazolin-5-ones and 2-amino-4(4′-methylphenyl)-thiazole. E-J Chem 7:1396–1406

    Article  CAS  Google Scholar 

  • Thore SN, Gupta SV, Bhahetui KG (2013) Synthesis and pharmacological investigation of novel substituted thiazole derivatives as non-carboxylic, anti-inflammatory and analgesic agents. Med Chem Res 23:3802–3811

    Article  Google Scholar 

  • Todeschini R, Gramatica P (1998) New 3D molecular descriptors: the WHIM theory and QSAR applications. Perspect Drug Discov Des 9–11:355–380

    Article  Google Scholar 

  • Tong J, Zhao X, Zhong L (2014) QSAR studies of imidazo[4,5-b]pyridine derivatives as anticancer drugs using RASMS method. Med Chem Res 23:4883–4892

    Article  CAS  Google Scholar 

  • Tropsha A (2010) Best practices for QSAR model development, validation, and exploitation. Mol Inform 29:476–488

    Article  CAS  Google Scholar 

  • Usui T, Ban HS, Kawada J, Hirokawa T, Nakamura H (2008) Discovery of indenopyrazoles as EGFR and VEGFR-2 tyrosine kinase inhibitors by in silico high-throughput screening. Bioorg Med Chem Lett 18:285–288

    Article  CAS  PubMed  Google Scholar 

  • Wang HH, Qiu KM, Cui HE, Yang YS, Yin-Luo Xing M, Qiu XY, Bai LF, Zhu HL (2013) Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents. Bioorg Med Chem 21:448–455

    Article  CAS  PubMed  Google Scholar 

  • Yan Z, Caldwell GW, Gauthier D, Leo GC, Mei J, Ho CY, Jones WJ, Masucci JA, Tuman RW, Galemmo RA, Johnson DL (2006) N-Glucuronidation of the platelet-derived growth factor receptor tyrosine kinase inhibitor 6,7-(dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine by human UDP-Glucuronosyltransferases. Drug Metab Dispos 34:748–755

    Article  CAS  PubMed  Google Scholar 

  • Yap CW (2011) An open source software to calculate molecular descriptors and fingerprints. J Comput Chem 32:1466–1474

    Article  CAS  PubMed  Google Scholar 

  • Yue EW, DiMeo SV, Higley CA, Markwalder JA, Burton CR, Benfield PA, Grafstrom RH, Cox S, Muckelbauer JK, Smallwood AM, Chen H, Chang C, Trainor GL, Seitz SP (2004) Synthesis and evaluation of indenopyrazoles as cyclin-dependent kinase inhibitors. Part 4: heterocycles at C3. Bioorg Med Chem Lett 14:343–346

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the financial support from University Grants Commission, New Delhi, India.

Author information

Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science & Technology, Hisar, Haryana, 125001, India

    Satbir Mor & Savita Nagoria

  2. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science & Technology, Hisar, Haryana, 125001, India

    Ashwani Kumar

  3. Department of Urology, Postgraduate Institute of Medical Education and Research, Chandigarh, 160012, India

    Jitender Monga

  4. Department of Pharmacy, Jaypee University of Information Technology, Solan, Himachal Pradesh, 173234, India

    Sandeep Lohan

Authors
  1. Satbir Mor
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Savita Nagoria
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ashwani Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jitender Monga
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sandeep Lohan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Satbir Mor.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2702 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mor, S., Nagoria, S., Kumar, A. et al. Convenient synthesis, anticancer evaluation and QSAR studies of some thiazole tethered indenopyrazoles. Med Chem Res 25, 1096–1114 (2016). https://doi.org/10.1007/s00044-016-1528-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-016-1528-8

Keywords

Search

Navigation