Skip to main content
SpringerLink
Log in

Carbazole Alkaloids IV

  • Chapter
Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

The European dye stuff industry originally provided the main stimulus for development of the chemistry of carbazoles since the discovery of the first member of the group, carbazole (1) from coal tar in 1872 by Graebe and Glazer (35). The isolation of carbazole as a degradation product of strychnine (2) by Clemo and Perkin (18) in 1924 provided further impetus for progress in the chemistry of carbazoles. N-Vinylcarbazole (3) was subsequently synthesised (12) and polymers based on vinyl carbazoles were developed subsequently (95) with the dye stuff industries and polymer industry contributing largely to further development of the chemistry of carbazoles up to 1960. The discovery of the first naturally occurring carbazole, the alkaloid murrayanine (4)* from Murraya koinigii Spreng; may be considered a further landmark in development of the chemistry and biology of carbazoles; the report on its structure was, however, published only in 1965 (12). Carbazole, methylcarbazole and dimethylcarbazole were isolated from soil humus in 1967 by Haworth et al. (14). More recently there has been added interest in the chemistry of carbazoles due to their use in electrophotography and related areas.

Deceased July 24, 2000

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bhattacharyya P, Chakraborty DP (1987) Carbazole Alkaloids. In: Herz W, Grisebach H, Kirby GW (eds) Fortschr Chem Organ Naturstoffe, Vol 52, p 159. Springer-Verlag, Wien, New York

    Google Scholar 

  2. Birch AJ, Leipa AJ, Stephenson GR (1979) Organometallic Compounds in Organic Synthesis: Some Tricarbonyl (Cyclohexadienyl) Iron Cations and Nitrogen Containing Nucleophils. Tetrahedron Lett 3565

    Google Scholar 

  3. Broka CA (1996) Eur Pat EP 695–755, US Pat 286043/1994 [(CA 124, 28951 (1996)]

    Google Scholar 

  4. Bush JA, Long BH, Catino JJ, Brander WT, Tomita K (1987) Production and Biological Activity of Rebeccamycin, a Novel Antitumour Agent. J Antibiot 40: 668

    CAS  Google Scholar 

  5. Carruthers W, Evans N (1974) Photocyclisation of Stryrylindole. Synthesis of 1-, 2-, 3- and 4-Methyl-11H-benzo [a] carbazoles. J Chem Soc Perkin 1, 421

    Google Scholar 

  6. Chaichatipyuth C, Pummangure S, Naowseran K, Thanyavuthi D, Anderson J, McLaughlin JL (1988) Two New Bioactive Carbazole Alkaloids from the Root Bark of Clausena harmandiana. J Nat Prod 51: 1285

    Google Scholar 

  7. Chakraborty A, Nath AC, Khasnobis S, Chakraborty M, Kored Y, Harigaya Y, Komiyana K (1997) Carbazole Alkaloids from Murraya koenigii. Phytochemistry 46: 751

    Google Scholar 

  8. Chakraborty A, Chowdhury BK, Bhattacharyya P (1995) Clausenol and Clausenine, Two Carbazole Alkaloids from Clausena anisata. Phytochemistry 40: 295

    CAS  Google Scholar 

  9. Chakraborty A, Saha C, Poddar G, Chowdhury BK, Bhattacharyya P (1995) Carbazole Alkaloid with Antimicrobial Activity from Clausena heptaphylla. Phytochemistry 38: 787

    CAS  Google Scholar 

  10. Chakraborty DP (1977) Carbazole Alkaloids. In: Herz W, Grisebach H, Kirby GW (eds) Fortschr Chem Organ Naturstoffe, Vol 34, p 299. Wien-New York: Springer

    Google Scholar 

  11. Chakraborty DP (1993) Chemistry and Biology of Carbazole Alkaloids. In: Cordell GA (ed) Alkaloids, Vol 44, p 257. New York: Academic Press

    Google Scholar 

  12. Chakraborty DP, Barman BK, Bose PK (1965) On the Constitution of Murrayamine, A Carbazole Derivative Isolated from Murraya koenigii Spreng. Tetrahedron 21: 681

    CAS  Google Scholar 

  13. Chakraborty DP, Roy S (1991) Carbazole Alkaloids III. In: Herz W, Kirby GW, Steglich W, Tamm Ch (eds) Fortschr Chem Organ Naturstoffe, Vol 57, p 71. Wien-New York: Springer

    Google Scholar 

  14. Chesire MK, Cranwell PK, Falshaw FF, Floyd AJ, Haworth RD (1967) Humic Acid-II, Structure of Humic Acids. Tetrahedron 23: 1669

    Google Scholar 

  15. Chunchatprasert L, Rao KRN, Shanon PV (1992) A New Synthetic Route to Pyrrolo[3, 2-b]-carbazoles, 1H-Benzofuro-[3, 2-fl-indole and 1H-[l] Benzo-thieno-[2,3 f-] indoles. J Chem Soc Perkin 1: 1779

    Google Scholar 

  16. Chunchatprasert L, Shanon PVR (1994) Further Observations on Novel Products from Acid Catalysed Indole-Pyrrole Condensation. Formation of Pyrrolo-[2, 3-bi. carbazole. J Chem Soc Perkin 1: 1965

    Google Scholar 

  17. Clemo GR, Perkin Jr WH, Robinson R (1927) Strychnine and Brucine, Part IV. J Chem Soc 1589

    Google Scholar 

  18. Clemo GR, Perkin Jr WH (1924) Vinyl Derivatives Specially of Carbazoles and Tetrahydro Carbozole and Their Behavior with Acids. J Chem Soc 115: 1804

    Google Scholar 

  19. Clive DLG, Et Kin N, Joseph T, Lown JW (1993) Synthesis of Carbazomycin B. J Org Chem 58: 2442

    CAS  Google Scholar 

  20. Dale JA, Mosher HS (1973) Nuclear Magnetic Resonance Enantiomer Reagents. Configurational Correlations via Nuclear Magnetic Resonance, Chemical Shifts of Diastereomeric Mandelet, 0-Methyl Mandelet and a-Methoxy-a-trifuromethylphenylacetate (MTPA) Esters. J Amer Chem Soc 95: 512

    CAS  Google Scholar 

  21. Danheiser RL, Brisbois RG, Kowalczyk JJ, Miller RK (1990) An Annulation Method for the Synthesis of Highly Substituted Polycyclic Aromatic and Heteroaromatic Compounds. J Amer Chem Soc 112: 3093

    CAS  Google Scholar 

  22. De Silva SO, Snieckus V (1974) The Witting Synthesis and Photo-cyclodehydrogenation of 3-(2-Aryl)-vinyl Indole Derivatives. Can J Chem 52: 1294

    Google Scholar 

  23. De Silva SO, Snieckus V (1974) Photochemical Synthesis of Benzo-[c]-carbazole and Pyridocarbazoles. Synthesis 254

    Google Scholar 

  24. Dillman RL, Cardellina JH (1991) Aromatic Secondary Metabolites from the Sponge Tednia ignis. J Nat Products 51: 1056

    Google Scholar 

  25. Erdtman H (1969) In: Harborne JB, Swain T (eds) Perspectives in Phytochemistry, p. 107. New York: Academic Press

    Google Scholar 

  26. Fiebig NJM, Soejarts DD, Kinghorn AD (1985) Koenoline, a Further Cytotoxic Carbazole Alkaloid from Murraya koenigii. Phytochemistry 24: 3041

    CAS  Google Scholar 

  27. Ferris RM, Tang FLM, Chang KJ, Russel A (1986) Evidence that the Potential Antipsychotic Agent Rincazole (BW234U) is Specific Competitive Antagonistic of Sigma Sites in Brain. Life Science 38: 2329

    CAS  Google Scholar 

  28. Furukawa H, Wu TS, Kuch C (1985) Structure of Murrafoline-B and -C, New Binary Carbazole Alkaloids from Murraya euchrestifolia. Chem Pharm Bull 33: 2613

    Google Scholar 

  29. Furukawa H, Wu TS, Kuch C (1985) Chemical Constituents of Murraya euchrestifolia Hayata. Structure of Novel Carbazoquinones and Other New Carbazole Alkaloids. Chem Pharm Bull 33: 4132

    CAS  Google Scholar 

  30. Furukawa H, Ito C, Wu TS, Mephail AT (1993) Structural Elucidation of Murrafolines, Six Novel Binary Carbazole Alkaloids Isolated from Murraya euchrestifolia. Chem Pharm Bull 41: 1249

    CAS  Google Scholar 

  31. Furukawa H, Ito C, Yogo M, Wu TS (1985) Structure of Murrayastine, Murrayaline and Pyrayafoline, Three New Carbazole Alkaloids from Murraya euchrestifolia. Chem Pharm Bull 33: 1320

    CAS  Google Scholar 

  32. Furukawa H, Ito C, Yogo M, Wu TS (1986) Synthesis of Pyrafoline B. Chem Pharm Bull 34: 2672

    CAS  Google Scholar 

  33. Furusaki A, Hashiba N, Matsumoto T, Hirano A, Iwai Y, Omura S (1978) X-Ray Crystal Structure of Staurosporine: A New Alkaloid from a Streptomyces Strain. J Chem Soc Chem Comm: 800

    Google Scholar 

  34. Golik J, Doyle TW, Krishnan B, Dubay G, Matson JA (1989) AT 2433-A 1, AT 2433A2, AT 2433-B1, and AT 2433-B2, Novel Antitumour Compounds Produced by Actinomadura melliaura, II. Structure Determination. J Antibiot 42: 1785

    Google Scholar 

  35. Gould ST, Tamay N, Meville CR, Cone MC (1994) Revised Structures for Kinamycin Antibiotics: 5-Diazobenzo-(b)-fluorenes Rather than Benzo-(b)-carbazole Cyanamides. J Amer Chem Soc 116: 2207

    CAS  Google Scholar 

  36. Graede C, Glazer C (1872) Über Carbazol. Chem Ber 5: 12

    Google Scholar 

  37. Hibino S, Tonari A, Chosi T, Suigino E (1993) New Approach to Antibiotic Carbazomycins: The Formal Total Synthesis of Carbazomycins-A and -B. Heterocycles 35: 441 (CA.119,49705Y, 1993)

    Google Scholar 

  38. Hino T, Nagawa M (1988) In: Brossi A (ed) ‘The Alkaloids’, Vol 34, p 1. San Diego: Academic Press

    Google Scholar 

  39. Hughes I, Raphael RA (1983) Synthesis of Arcyriaflavin B. Tetrahedron Lett 24: 1441

    CAS  Google Scholar 

  40. Husson HP, Thal C, Potier P, Wenkert E (1970) Photocyclisation of l-(a-Indolyl)2(3-pyridyl)-acrylonitrile. J Org Chem 35: 442

    CAS  Google Scholar 

  41. Ignatiaias I, Dorbas M, Appino A (1986) Identification of Carbazole Derivatives in a Hydrotreated Gas Oil by Gas Chromatography and Gas Chromatography-Mass Spectrophotometry. J Chromatography 366: 251

    Google Scholar 

  42. Ito C, Furukawa H (1991) Structure of Murranimbine, A Novel Dimeric Carbazole Alkaloid from Murraya euchrestifolia. Chem Pharm Bull 39: 1355

    CAS  Google Scholar 

  43. Ito C, Furukawa H (1990) New Carbazole Alkaloid from Murraya euchrestifolia. Chem Pharm Bull 38: 1548

    CAS  Google Scholar 

  44. Ito C, Ohta H, Tan HTW, Furukawa H (1996) Constituents of Clausena excavata, Isolation and Structural Elucidation of Seven New Carbazole Alkaloids and a New Coumarin. Chem Pharm Bull 44: 2231

    CAS  Google Scholar 

  45. Ito C, Nakagawa M, Wu T-S, Furukawa H (1991) New Carbazole Alkaloids from Murraya euchrestifolia. Chem Pharm Bull 39: 1668

    CAS  Google Scholar 

  46. Ito C, Nakagawa M, Wu T-S, Furukawa H (1991) New Carbazole Alkaloids from Murraya euchrestifolia. Chem Pharma Bull 39: 2525

    CAS  Google Scholar 

  47. Ito C, Okahana N, Wu T-S, Wang ML, Lai JS, Khon CS, Furukawa H (1992) New Carbazole Alkaloids from Murraya euchrestifolia. Chem Pharm Bull 40: 230

    CAS  Google Scholar 

  48. Ito C, Katsuno S, Ohta H, Omura M, Kajiura I, Furukawa H (1997) Constituents of Clausena excavata. Isolation and Structure Elucidation. Chem Pharm Bull 45: 48

    CAS  Google Scholar 

  49. Ito C, Wu T-S, Furukawa H (1990) Novel Binary Carbazole Alkaloids from Murraya euchrestifolia. Chem Pharm Bull 38: 1143

    CAS  Google Scholar 

  50. Ito C, Thoyama Y, Omura M, Kajiura I, Furukawa H (1993) Alkaloidal Constituents of Murraya koenigii. Isolation and Structural Elucidation of Novel Binary Carbazoloquinone and Carbazole Alkaloids. Chem Pharm Bull 44: 2096

    Google Scholar 

  51. Jackson PM, Moody CJ, Mortimer RJ (1991) Synthesis and Electro-chemical Properties of Naturally Occurring Free Radical Scavenger Carazostatin. J Chem Soc Perkin 1: 2941

    Google Scholar 

  52. Kadiri A, Fadouch M, Benali B, Boucetta A (1994) The Effects of Complexation by Hydrogen Bonds and N-Ethylation on UV Absorption Spectra of Carbazoles. Spectrochim Acta 50A: 851 (C.A. 1994, 120: 3222638)

    CAS  Google Scholar 

  53. Kaneda M, Kitahara T, Yamasaki K, Nakamura S (1990) Biosynthesis of Carbazomycin B, II: Origin of Whole Carbon Skeleton. J Antibiotics 43: 1623

    CAS  Google Scholar 

  54. Kaneko T, Wong H, Okamoto KT, Clardy J (1986) Two Synthetic Approaches to Rebeccamycin. Tetrahedron Lett 26: 4015

    Google Scholar 

  55. Kano S, Sugino E, Shibuya S, Hibino S (1981) A New Synthesis of Antitumour 6-HPyrido-[4, 4-b1-Carbazole Alkaloid, Elipticine. J Org Chem 46: 2979

    CAS  Google Scholar 

  56. Kano S, Sugino E, Shibuya S, Hibino S (1987) Synthesis of Carbazole Alkaloids Hyellazole and 6-Chlorohyellazole. J Org Chem 46: 3856

    Google Scholar 

  57. Kapil RS (1971) In: Manske RHF (ed) ‘The Alkaloids’, Vol 12, p 273. New York-London: Academic Press

    Google Scholar 

  58. Kase H, Ewahasi K, Matsuda Y (1986) K252a, A Potent Inhibitor of Protein Kinase C from Microbial Origin. J Antibiot 39: 1019

    Google Scholar 

  59. Kato S, Kawai H, Kawasaki T, Toda Y, Urata T, Hayakawa Y (1989) Studies of Free Radical Scavenging Substances from Microorganisms, I: Carazostatin. A New Free Radical Scavenger Produced by Streptomyces chromgfuccus DC 118. J Antibiot 42: 1879

    CAS  Google Scholar 

  60. Kawasaki T, Sakamoto M (1994) Electrocyclisation for Synthesis of Carbazoles and Their Annulated Compounds. J Indian Chem Soc 71: 443 and references cited therein

    Google Scholar 

  61. Kazano S, Mosahiro, Kanno F, Yoichi H, Hamo S (1986) Structure of Carazostatin, A Neutral Cell Promoting Substance Produced by Streptomyces. J Antibiot 39: 1059

    Google Scholar 

  62. Kinoshita J, Tatara S, Sankawa U (1985) Structures of Paniculadins A and B, Novel Phenylindoles from Murraya paniculata. Chem Pharm Bull 33: 1770

    CAS  Google Scholar 

  63. Kinoshita J, Tatara S, Yamasaki K, Nakamura S (1990) Biosynthesis of Carbazomycin B, III. J Anbibiot 43: 1623

    Google Scholar 

  64. Knolker H-J (1995) Transition Metal-mediated Synthesis of Carbazole Derivatives. In: Advances in Nitrogen Heterocycles 1: 173. JAI Press Inc and references cited therein

    Google Scholar 

  65. Knolker H-J, Bauermeister M (1989) The Total Synthesis of Carbazole Antibiotic Carbozomycin B and an Improved Route to Carbazomycin A. J Chem Soc Chem Comm 1468

    Google Scholar 

  66. Knolker H-J, Bauermeister M (1990) Iron-Mediated Total Synthesis of the Cytotoxic Carbazole Koenoline and Related Alkaloids. J Chem Soc Chem Comm 664

    Google Scholar 

  67. Knolker H-J, Wolpert M (1997) Transition Metal Complexes in Organic Synthesis, Part 36, Cyclization of Tricarbony1 Iron Complexes by Oxygen to 4a,9a-Dihydro-9Hcarbazoles: Applications to the Synthesis of Mukonine, Mukonidine and Pyrido[3, 2, 1-JI-carbazoles. Tetrahedron Lett 38: 533

    Google Scholar 

  68. Kumar V, Wickramasinghe DBM, Jacobson U (1990) lndole Dimer from Murraya gleni. Tetrahedron Lett 31: 5217

    CAS  Google Scholar 

  69. Kumar V, Reisch J, Wickramasinghe A (1989) Glycomaurin and Glycomaurol, New Carbazole Alkaloids from G. mauritiana Bark. Aust J Chem 42: 1375

    CAS  Google Scholar 

  70. Kusano G, Sibano M, Idoji M, Minoura K (1993) A New Alkaloid 2-Hydroxy-7methyl-9H Carbazole from Cimicifuga simplex. Heterocycles 136: 2367

    Google Scholar 

  71. Ljunggren BO, Lundberg K (1985) In vivo Phototoxicity of Nonsteroidal Anti-inflammatory Drugs Evaluated by the Mousetail Technique. Photodermatology 2: 377 (C.A. 104 1986 81699a)

    Google Scholar 

  72. Li WS, Mechesney JD, El-Feraly FG (1991) Carbazole Alkaloids from Clausena lansium. Phytochemistry 30: 343

    CAS  Google Scholar 

  73. Luk KL, Stern L, Weigel M, O’Brien RA, Spirit N (1983) Isolation and Identification of ‘Diazepam’-like Compounds from Bovine Urine. J Nat Prod 46: 852

    CAS  Google Scholar 

  74. Magnus PD, Sear NL (1984) Indole-2, -3 Quinodimethanes, Synthesis of Selectively Protected Derivatives of Fused Dimeric Indole Alkaloid Staurosporine. Tetrahedron 40: 2795

    CAS  Google Scholar 

  75. Martin T, Moody CJ (1985) Synthesis of Carbazole Alkaloid Murrayaquinone B. J Chem Soc Chem Commun: 1391

    Google Scholar 

  76. Matson JA, Claridge C, Bush JA, Titus J, Bradner WT, Doyle TW, Horan AC, Patel M (1989) AT 2433-A1, AT 2433-A2, AT 2433-B1 and AT 2433-B2, Novel Antitumour Antibiotic Compounds Produced by Actinomadura melliaura, Taxonomy, Fermentation, Isolation and Biological Properties. J Antibiot 42: 1547

    CAS  Google Scholar 

  77. Meksuriyen D, Cordell GA (1988) Biosynthesis of Staurosporine 2. Incorporation of Tryptophan. J Nat Prod 51: 893

    CAS  Google Scholar 

  78. Mitra AR (1974) PhD Thesis, Calcutta University

    Google Scholar 

  79. Mithani S, Weeratunga G, Taylor NJ, Dimitrierienko GI (1994) The Kinamycins are Diazofluorens and not Cyanocarbazoles. J Amer Chem Soc 116: 2209

    Google Scholar 

  80. Moody CJ, Shah P (1989) Diels-Alder Reactivity of Pyrano-j3, 4-b]-indole-3-ones, Synthesis of Carbazoles Carbazomycin-A, -B and Hyellazole. J Chem Soc Perkin 1, 2463

    Google Scholar 

  81. Morioka H, Ishahara M, Shibai H, Suzuki T (1985) Agri Biol Chem 49: 1959

    Google Scholar 

  82. Morioka H, Shibai H, Yokagawa Y, Ishahara M, Kida T, Suzuki T (C.A. 104 1986, 18649u)

    Google Scholar 

  83. Morris GA, Freeman R (1979) Enhancement of Nuclear Magnetic Resonance Signals by Polarization Transfer. J Amer Chem Soc 101: 760

    CAS  Google Scholar 

  84. Mudry CA, Frasca AR (1974) Photochemical Reductions of 2,3-Diphenyl Indoles. Tetrahedron 30: 2983

    CAS  Google Scholar 

  85. Nagadjui BT, Ayafor JF, Sondongam BL, Connolly JD (1989) Quinolone and Carbazole Alkaloids from Clausena anisata. Phytochemistry 28: 1517

    Google Scholar 

  86. Nakanishi S, Matsuda Y, Iwahasi K, Kase H (1986) K-252a, b, c and d, Potent Inhibitors of Protein Kinase C from Microbial Origin. Antibiot 39: 1066

    CAS  Google Scholar 

  87. Nettleton DE, Doyle TW, Krishnan B, Matsumoto GK, Clardy J (1985) Isolation and Structure of Rebeccamycin¡ªA New Antitumour Antibiotic from Nocardia aerocoligenes, Tetrahedron 26: 4011

    CAS  Google Scholar 

  88. Omura S, Nakagawa A, Yamada H, Hata T, Furusaki A, Watanabe T (1971) Structure of Kinamycin C and Structural Relations Among Kinamycin A, B, C, D. Chem Pharm Bull 19: 2428

    CAS  Google Scholar 

  89. Omura S, Iwai Y, Hirano A, Nakagawa A, Awaya J, Suchiya HT, Takahashi Y, Masuma R (1977) A New Alkaloid AM-2282 of Streptomyces Origin: Taxonomy, Fermentation, Isolation and Preliminary Characterisation. J Antibiot 30: 275

    CAS  Google Scholar 

  90. Patterson AM, Capbell LT (1940) The Ring Index P 229 No 1675. New York: Reinhold

    Google Scholar 

  91. Pearce CJ, Doyle TW, Forenza S, Lem KS, Schroeder DS (1988) The Biosynthetic Origin of Rebeccamycin. J Nat Prod 51: 937

    CAS  Google Scholar 

  92. Pindur U, Erfauion-Ardoust H (1989) Indole-2,3-quinodimethanes and Stable Cyclic Analogues for Regio-and Stereo-controlled Synthesis of (b) Annealated Indoles. Chem Rev 89: 1681

    CAS  Google Scholar 

  93. Pindur U, Adam R (1991) 1,6-Electrocyclisation Reaction of Acceptor Substituted 2,3-Vinylindoles to Functionalised Carbazole. Heterocycles 31: 581

    Google Scholar 

  94. Pointek JA, Wang RY (1986) Acute and Subchronic Effects of Rincazole (B234U) a Potential Antipsychotic Drug on A9 and A10 Dopamine Neurons in the Rat. Life Sci 39: 651

    Google Scholar 

  95. Ramesh K, Kapil RS (1986) Synthesis of Murrayafoline B and Murrayaquinone-B. Indian J Chem 25B: 462

    CAS  Google Scholar 

  96. Rice LM, Scot KB (1970) 3-Substituted 1,2,3,4-Tetrahydrocarbazoles. J Medicin Chem 13: 308

    CAS  Google Scholar 

  97. Reisch JO, Goz O, Wickramsinghe A, Baudra Herath HKT, Henkel G (1992) Carbazole Alkaloids from Seeds of Murraya koenigii. Phytochemistry 31: 2877

    CAS  Google Scholar 

  98. Reppe W, Stark W, Voss A (1934) Complex Polymerization Products (CA 28: 32556)

    Google Scholar 

  99. Roy S, Guha R, Ghosh S, Chakraborty DP (1982) Biomimetic Hydroxylation Studies on Carbazole Alkaloids. Ind J Chem 21B: 617

    CAS  Google Scholar 

  100. Ruangrungi N, Ariyapraycon J, Lang GL, Organ HG (1990) Three New Carbazole Alkaloids Isolated from Murraya siamensis. J Nat Prod 53: 946

    Google Scholar 

  101. Sarstedt B, Winterfeldt E (1983) Reactions with Indole Derivatives, XLVIII. Heterocycles 20: 469

    CAS  Google Scholar 

  102. Saroja B, Srinivasan PC (1986) Synthesis and (4+2) Cyclo Additions of N-(Phenylsulphonyl-3)-vinyl-indole. Synthesis: 748

    Google Scholar 

  103. Sato A, Morishita P, Shiraki T, Yoshioka S, Horikoshi H, Kaswano H, Hanzawa H, Hata T (1993) Aldose Reductase, Inhibitors from Marine Sponge Doctyodendri sp. J Org Chem 58: 7632

    CAS  Google Scholar 

  104. Sezaki M, Sasaki T, Nakazawa T, Takeda U, Iwata M, Watanabe T, Koyama M, Kai F, Shomura T, Kojima N (1985) A New Antibiotic SF-2370 Produced by Actinomadura sp. SF-2370. Antibiot 38: 1439

    Google Scholar 

  105. Shinya K, Tanaka M, Furihata K, Hayakawa Y, Seto H (1993) Structure of Carquinostatin A, A New Cell Protecting Substance Produced by Streptomyces exfoliates. Tetrahedron Lett 34: 4943

    CAS  Google Scholar 

  106. Steglich W, Steffan R, Kopanski L, Echardt G (1980) Archyriaflavin-B, -C, Angew Chem lnt Engl 19: 459

    Google Scholar 

  107. Takahashi I, Kobayashi E, Asano K, Yoshida M, Nakano H (1987) UCN-0I, A Selective Inhibitor of Protein Kinase C from Streptomyces. J Antibiot 40: 1782

    CAS  Google Scholar 

  108. Takeya K, Itoigawa M, Furukawa H (1989) Triphasic Inotropic Response of Muscle to Murrayaquinone. Isolated from Rutaceae. Eur J Pharmacol 169: 137

    CAS  Google Scholar 

  109. Tamaoki T, Nomoto H, Takahasi I, Kato Y, Morimoto N, Tomita P (1986) Staurosporine, A Potent Inhibitor of Phospholipid/Ca++ Dependent Protein Kinase. Biochem Biophys Res Commun 135: 397

    CAS  Google Scholar 

  110. Tanida S, Takizawa M, Takahashi T, Tsubotani S, Harda S (1989) Tan-999 and Tan-1030A. New Indole Carbazole Alkaloids with Macrophage Activating Properties. J Antibiot 42: 1619

    CAS  Google Scholar 

  111. Taylor MR, Westwood SA (1993) An Investigation of Drug Detection in Equine Urine Samples by Modern TLC. J Planar Chromatography and TLC 6: 415

    CAS  Google Scholar 

  112. Te Paske MR, Gloer JB, Wicklow DT, Dowd PF (1990) Aflavazole: A New Antiinsectant Carbazole Metabolite from Sclerotia of Aspergllius flavus. J Org Chem 55: 5299

    Google Scholar 

  113. Te Paske MR, Gloer JB, Wicklow DT, Dowd PF (1989) An Antiviral Carbazole Alkaloid from Sclerotia of Aspergillus tubingensis. J Org Chem 54: 4743

    Google Scholar 

  114. Te Paske MR, Gloer JB, Wicklow DT, Dowd PF (1989) Structure of Tubingensin B, A Cytotoxic Carbazole Alkaloid from Sclerotia of Aspergillus tubingensis. Tetrahedron 45: 4961

    Google Scholar 

  115. Tsubotani S, Tanida S, Harda S (1991) Structure Determination of Indolocarbazole Alkaloids by NMR Spectroscopy. Tetrahedron 47: 3565

    CAS  Google Scholar 

  116. Wada A, Hirai S, Hanaoka M (1994) Novel Synthesis of Quinazolinequinone and Carbazoloquinone Through Anionic Cycloaddition: Its Application to Murrayaquinone A. Chem Pharm Bull 42: 416

    CAS  Google Scholar 

  117. Weinreb SM, Garigipati RS, Gainor JA (1984) Natural Product Synthesis via Cycloaddition with N. Sulfinyl Dienophiles. Heterocycles 21: 309

    CAS  Google Scholar 

  118. Wu T-S (1991) Murrayamine A, B, C and (+)-Mahanine, Carbazole Alkaloids from Murraya euchrestifolia. Phytochemistry 30: 1048

    CAS  Google Scholar 

  119. Wu T-S, Wang M-L, Lai J-S, Ito C, Furukawa H (1991) Binary Carbazole Alkaloids from Murraya euchrestifolia. Phytochemistry 30: 1054

    Google Scholar 

  120. Yang W, Jiang T, Davis PT, Acosta D (1991) In vitro Metabolism and Toxicity Assessment of N-Methyl Carbazole in Primary Culture Rat Hepatocytes. Toxicology 68: 217 (C.A. 115 225969, 1991)

    Google Scholar 

  121. Yamasaki K, Kaneda M, Watanabe K, Ueki Y, Ishamari K, Nakamura S, Nomi R, Yoshida N, Nakajima T (1983) New Antibiotics Carbazomycin A and B, Ill. J Antibiot 36: 552

    CAS  Google Scholar 

  122. Yasuzawa T, Iada T, Yoshida M, Hirayama N, Takahashi M, Shirahata K, Sano H (1986) The Structures of Novel Protein Kinase C. Inhibitors K-252a, -b, -c, and -d. J Antibiot 39: 1072

    CAS  Google Scholar 

  123. Yogo M, Ito C, Furukawa H (1991) Synthesis of Some Carbazoloquinone Alkaloids and Their Analogues, Facile pelladium Assisted Intramolecular Ring Closure of Arylamino-1,4-Benzoquinones to Carbazole-1,4-quinones. Chem Phar Bull 39: 328

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Natural Products, Calcutta, India

    D. P. Chakraborty

  2. Calcutta, India

    Shyamali Roy

Authors
  1. D. P. Chakraborty
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shyamali Roy
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 2003 Springer-Verlag Wien

About this chapter

Cite this chapter

Chakraborty, D.P., Roy, S. (2003). Carbazole Alkaloids IV. In: Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 85. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6051-0_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-6051-0_3

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7290-2

  • Online ISBN: 978-3-7091-6051-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation