Indole compounds against breast cancer: Recent developments

Current Drug Targets

Volumn 13, Issue 14, 2012, Pages 1705-1719

  Biersack, Bernhard ^a   Schobert, Rainer ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Anticancer drugs; Breast cancer; DIM; Indole; Kinase inhibitors; Protein binders; Tubulin

Indexed keywords

3 INDOLEMETHANOL; 3 O PENTYL BENZODIAZEPINE; 3, 3' DIINDOLYLMETHANE; 4 O PENTYL BENZODIAZEPINE; BENZODIAZEPINE DERIVATIVE; COMBRETASTATIN; DOCETAXEL; DOXORUBICIN; ELLIPTICINE; ENZASTAURIN; ESTROGEN RECEPTOR ALPHA; FUMITREMORGIN C; GOLD COMPLEX; GROWTH INHIBITOR; INDIRUBIN; INDOLE DERIVATIVE; ISATIN; MITOMYCIN; MOTESANIB; NOCODAZOLE; PANOBINOSTAT; PROTEIN KINASE INHIBITOR; SUNITINIB; TAMOXIFEN; TOPOTECAN; TRASTUZUMAB; TUBULIN MODULATOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE; VINCA ALKALOID;

APOPTOSIS; BIOSYNTHESIS; BRASSICA; BREAST CANCER; CARDIOTOXICITY; CELL CYCLE; CELL MIGRATION; COLON CANCER; DRUG ACTIVITY; DRUG EXPOSURE; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; IC 50; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PHASE 3 CLINICAL TRIAL (TOPIC); REVIEW; TUMOR REGRESSION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOLOGICAL AGENTS; BREAST NEOPLASMS; FEMALE; HUMANS; INDOLES;

EID: 84873901776     PISSN: 13894501     EISSN: 18735592     Source Type: Journal    
DOI: 10.2174/138945012804545551     Document Type: Review

References (101)

1. Johnson IS, Armstrong JG, Gorman M, Burnett JP. The vinca alkaloids: a new class of oncolytic agents. Cancer Res 1963; 23: 1390-427.
2. Omura S, Iwai Y, Hirano A, et al. A new alkaloid AM-2282 of Streptomyces origin taxonomy, fermentation, isolation and preliminary characterization. J Antibiot 1977; 30: 275-82.
3. Barrios CH, Liu M-L, Lee SC, et al. Phase III randomized trial of sunitinib versus capecitabine in patients with previously treated HER2-negative advanced breast cancer. Breast Cancer Res Treat 2010; 121: 121-31.
4. Mina L, Krop I, Zon RT, et al. A phase II study of oral enzastaurin in patients with metastatic breast cancer previously treated with an anthracycline and a taxane containing regimen. Invest New Drugs 2009; 27: 565-70.
5. Boger DL, Johnson DS. CC-1065 und die Duocarmycine: mechanistische Studien zum Verständnis ihrer biologischen Funktion. Angew Chem 1996; 108: 1542-80.
6. Sarkar FH, Li Y. Harnessing the fruits of nature for the development of multi-targeted cancer therapeutics. Cancer Treat Rev 2009; 35: 597-607.
7. Curigliano G, Goldhirsch A. The triple-negative subtype: New ideas for the poorest prognosis breast cancer. J Natl Cancer Inst 2011; 43: 108-10.
8. Foulkes WD, Stefansson IM, Chappuis PO, Bégin LR, Goffin JR, Wong N, Trudel M, Akslen M, Akslen LA. Germline BRCA1 mutations and a basal epithelial phenotype in breast cancer. J Natl Cancer Inst 2003; 95: 1482-5.
9. Ahmad A, Sakr WA, Rahman KMW. Mechanisms and therapeutic implications of cell death induction by indole compounds. Cancers 2011; 3: 2955-74.
10. Jump SM, Kung J, Staub R, et al. N-Alkoxy derivatization of indole- 3-carbinol increases the efficacy of the G1 cell cycle arrest and of I3C-specific regulation of the cell cycle gene transcription and activity in human breast cancer cells. Biochem Pharmacol 2008; 75: 713-24.
11. Nguyen HH, Lavrenov SN, Sundar SN, et al. 1-Benzyl-indole-3- carbinol is a novel indole-3-carbinol derivative with significantly enhanced potency of anti-proliferative and anti-estrogenic properties in human breast cancer cells. Chemico-Biological Interactions 2010; 186: 255-66.
12. Guo W, Wu S, Liu J, Fang B. Identification of a small molecule with synthetic lethality for K-Ras and Protein Kinase C Iota. Cancer Res 2008; 68: 7403-8.
13. Wu S, Wang L, Guo W, et al. Analogues and derivatives of oncrasin- 1, a novel inhibitor of the C-terminal domain of RNA polymerase II and their antitumor activities. J Med Chem 2011; 54: 2668-79.
14. Safe S, Papineni S, Chintharlapalli S. Cancer chemotherapy with indole-3-carbinol, bis(3'-indolyl)methane and synthetic analogues. Cancer Lett 2008; 269: 326-38.
15. Li W-S, Wang C-H, Ko S, et al. Synthesis and evaluation of the cytotoxicities of tetraindoles: observation that the 5-hydroxy tetraindole (SK228) induces G2 arrest and apoptosis in human breast cancer cells. J Med Chem 2012; 55: 1583-92.
16. Kamal A, Srikanth YVV, Khan NA, Shaik TB, Ashraf M. Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity. Bioorg Med Chem Lett 2010; 20: 5229-31.
17. Reddy BVS, Rajeswari N, Sarangapani M, Prashanti Y, Ganji RJ, Addlagatta A. Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity. Bioorg Med Chem Lett 2012; 22: 2460-3.
18. Kamal A, Srikanth YVV, Ramaiah MJ, et al. Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[ 2,1-c][1,4]benzodiazepine conjugates. Bioorg Med Chem Lett 2012; 22: 571-8.
19. Chao W-R, Yean D, Amin K, Green C, Jong L. Computer-aided rational drug design: a novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signalling. J Med Chem 2007; 50: 3412-5.
20. Andreani A, Burnelli S, Granaiola M, et al. Substituted E-3-(2- chloro-3-indolylmethylene)1,3-dihydroindol-2-ones with antitumor activity. Effect on the cell cycle and apoptosis. J Med Chem 2007; 50: 3167-72.
21. Singh P, Kaur M, Holzer W. Synthesis and evaluation of indole, pyrazole, chromone and pyrimidine based conjugates for tumor growth inhibitory activities - development of highly efficacious agents. Eur J Med Chem 2010; 45: 4968-82.
22. De Santi M, Galluzi L, Lucarini S, et al. The indole-3-carbinol cyclic tetrameric derivative Ctet inhibits cell proliferation via overexpression of p21/CDKN1A in both estrogen receptor-positive and triple-negative breast cancer cell lines. Breast Cancer Res 2011; 13: R33.
23. Kumar D, Kumar NM, Ghosh S, Shah K. Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents. Bioorg Med Chem Lett 2012; 22: 212-5.
24. Diana P, Carbone A, Barraja P, et al. 3,5-Bis(3'-indolyl)pyrrazoles, analogues of marine alkaloid nortopsentin: synthesis and antitumor properties. Bioorg Med Chem Lett 2007; 17: 6134-7.
25. Andreani A, Burnelli S, Granaiola M, et al. Antitumor activity of bis-indole derivatives. J Med Chem 2008; 51: 4563-70.
26. Andreani A, Burnelli S, Granaiola M, et al. Antitumor activity and COMPARE analysis of bis-indole derivatives. Bioorg Med Chem 2010; 18: 3004-11.
27. Ahn S, Hwang DJ, Barrett CM, Yang J, Duke III CB, Miller DD, Dalton JT. A novel bis-indole destabilizes microtubules and displays potent in vitro and in vivo antitumor activity in prostate cancer. Cancer Chemother Pharmacol 2011; 67: 293-304.
28. Li X, Zheng S-L, Li X, et al. Synthesis and anti-breast cancer activity of new indolylquinone derivatives. Eur J Med Chem 2012; doi: 10.1016/j.ejmech.2012.04.019
29. Milbank JBJ, Stevenson RJ, Ware DC, et al. Synthesis and evaluation of stable bidentate transition metal complexes of 1- (chloromethyl)-5-hydroxy-3-(5,6,7-trimethoxy-2-indol-2- ylcarbonyl)-2,3-dihydro-1H-pyrrolo[3,2-f]quinoline (seco-6- azaCBI-TMI) as hypoxia selective cytotoxins. J Med Chem 2009; 52: 6822-34.
30. Liu J, Zhao M, Qian K, et al. Benzyl 1,2,3,5,11,11a-hexahydro-3,3- dimethyl-1-oxo-6H-imidazo[3',4':1,2]pyrdin[3,4-b]indole-2- substituted acetatzes: one-pot-preparation, anti-tumor activity, docking toward DNA and 3D QSAR analysis. Bioorg Med Chem 2010; 18: 1910-7.
31. Chen Z, Cao R, Shi B, et al. Synthesis of novel β-carbolines with efficient DNA-binding capacity and potent cytotoxicity. Bioorg Med Chem Lett 2010; 20: 3876-9.
32. Stiborová M, Sejbal J, Borek-Dohalská L, et al. The anticancer drug ellipticine forms covalent DNA adducts, mediated by human cytochromes P450, through metabolism to 13-hydroxyellipticine and ellipticine N2-oxide. Cancer Res 2004; 64: 8374-80.
33. Shinkre BA, Raisch KP, Fan L, Velu SE. Analogs of the marine alkaloid makaluvamines: synthesis, topoisomerase II inhibition, and anticancer activity. Bioorg Med Chem Lett 2007; 17: 2890-3.
34. Li Z, Zhai F, Zhao L, Guo Q, You Q. Design and synthesis of Nmethylmaleimide indolocarbazole bearing 2-acetamino acid moieties as topoisomerase I inhibitors. Bioorg Med Chem Lett 2009; 19: 406-9.
35. Bacher G, Nickel B, Emig P, et al. D-24851, a novel synthetic microtubule inhibitor, exerts curative antitumoral activity in vivo, shows efficacy toward multidrug-resistant tumor cells, and lacks neurotoxicity. Cancer Res 2001; 61: 392-9.
36. Kaufmann D, Pojarova, Vogel S, et al. Antimitotic activities of 2- phenylindole-3-carbaldehydes in human breast cancer cells. Bioorg Med Chem 2007; 15: 5122-36.
37. Pojarová M, Kaufmann D, Gastpar R, Nishino T, Reszka P, Bednarski PJ, von Angerer E. [(2-Phenylindol-3-yl)methylene] propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis. Bioorg Med Chem 2007; 15: 7368-79.
38. Vogel S, Kaufmann D, Pojarová M, et al. Aroyl hydrazones of 2- phenylindole-3-carbaldehydes as novel antimitotic agents. Bioorg Med Chem 2008; 16: 6436-47.
39. Ahn S, Duke III CB, Barrett CM, Hwang DJ, Li C-M, Miller DD, Dalton JT. I-387, a novel antimitotic indole, displays a potent in vitro and in vivo antitumor activity with less neurotoxicity. Mol Cancer Ther 2010; 9: 2859-68.
40. Romagnoli R, Baraldi PG, Sarkar T, et al. Synthesis and biological evaluation of 1-methyl-2-(3',4',5'-trimethoxybenzoyl)-3-amino indoles as a new class of antimitotic agents and tubulin inhibitors. J Med Chem 2008; 51: 1464-8.
41. La Regina G, Sarkar T, Bai R, et al. New arylthioindoles and related bioisosters at the sulfur bridging group. 4. Synthesis, tubulin polymerization, cell growth inhibition, and molecular modeling studies. J Med Chem 2009; 52: 7512-27.
42. La Regina G, Bai R, Rensen W, et al. Design and synthesis of 2- heterocyclyl-3-arylthio-1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability. J Med Chem 2011; 54: 8394-406.
43. Li P-K, Xiao Z, Hu Z, et al. Conformationally restricted analogs of combretastatin A-4 derived from SU5416. Bioorg Med Chem Lett 2005; 15: 5382-5.
44. Andreani A, Burnelli S, Granaiola M, et al. Antitumor activity of substituted E-3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2- ones. J Med Chem 2006; 49: 6922-4.
45. Havrylyuk D, Kovach N, Zimenkovsky B, Vasylenko O, Lesyk R. Synthesis and anticancer activity of isatin-based pyrazolines and thiazolidines conjugates. Arch Pharm Chem Life Sci 2011; 344: 514-22.
46. Vine KL, Locke JM, Ranson M, Pyne SG, Bremner JB. An investigation into the cytotoxicity and mode of action of some novel Nalkyl substituted isatins. J Med Chem 2007; 50: 5109-17.
47. Matesic L, Locke JM, Bremner JB, et al. N-Phenethyl and Nnapththylmethyl isatins and analogues as in vitro cytotoxic agents. Bioorg Med Chem 2008; 16: 3118-24.
48. Reyes F, Fernández R, Rodríguez A, et al. Aplicyanins A-F, new cytotoxic bromoindole derivatives from the marine tunicate Aplidium cyaneum. Tetrahedron 2008; 64: 5119-23.
49. Shetty RS, Lee Y, Liu B, et al. Synthesis and pharmacological evaluation of N-(3-(1H-indol-4-yl)-5-(2-methoxyisonicotinoyl)phe nyl)methanesulfonamide (LP-261), a potent antimitotic agent. J Med Chem 2011; 54: 179-200.
50. Simoni D, Invidata FP, Eleopra M, et al. Design, synthesis and biological evaluation of novel stilbene-based antitumor agents. Bioorg Med Chem 2009; 17: 512-22.
51. Zhang Q, Peng Y, Wang XI, Keenan SM, Arora S, Welsh WJ. Highly potent triazole-based tubulin polymerization inhibitors. J Med Chem 2007; 50: 749-54.
52. Arora S, Wang XI, Keenan SM, et al. Novel microtubule polymerization inhibitor with potent antiproliferative and antitumor activity. Cancer Res 2009; 69: 1910-5.
53. Schobert R, Biersack B, Dietrich A, Effenberger K, Knauer S, Mueller T. 4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and -N-methylimidazoles that are cytotoxic against combretastatin A resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model. J Med Chem 2010; 53: 6595-6602.
54. Kemnitzer W, Drewe J, Jiang S, et al. Discovery of 4-aryl-4Hchromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structureactivity relationships of fused rings at the 7,8-positions. J Med Chem 2007; 50: 2858-64.
55. Kemnitzer W, Drewe J, Jiang S, et al. Discovery of 4-aryl-4Hchromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 4. Structureactivity relationships of N-alkyl substituted pyrrole fused at the 7,8- positions. J Med Chem 2008; 51: 417-23.
56. Gasparatto V, Castagliuolo I, Ferlin MG. 3-Substituted 7-phenylpyrroloquinolinones show potent cytotoxic activity in human cancer cell lines. J Med Chem 2007; 50: 5509-13.
57. Keller L, Beaumont S, Liu J-M, et al. New C5-alkylated indolobenzazepinones acting as inhibitors of tubulin polymerization: cytotoxic and antitumor activities. J Med Chem 2008; 51: 3414-21.
58. Putey A, Popowycz F, Do Q-T, et al. Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: synthesis and structure-activity relationship studies. J Med Chem 2009; 52: 5916-25.
59. Karaman MW, Herrgard S, Treiber DK, et al. A quantitative analysis of kinase inhibitor selectivity. Nat Biotech 2008; 26: 127-32.
60. Tevaarwerk A, Wilding G, Eickhoff J, et al. Phase I study of continuous MKC-1 in patients with advanced or metastatic solid malignancies using the modified time-to-extent continual reassessment method (TITE-CRM) dose escalation design. Invest New Drugs 2012; 30: 1039-45.
61. Wang K, Liu Z-Z. Synthesis of N-methyl-bisindolylmaleimide amino acid methyl ester conjugates andcytotoxicity study. Eur J Med Chem 2010; 45: 4175-9.
62. Burstein HJ, Elias AD, Rugo HS, et al. Phase II study of sunitinib malate, an oral multitargeted tyrosine kinase inhibitor, in patients with metastatic breast cancer previously treated with an anthracycline and a taxane. J Clin Oncol 2008; 26: 1810-6.
63. Telli ML, Witteles RM, Fisher GA, Srinivas S. Cardiotoxicity associated with the cancer therapeutic agent sunitinib malate. Ann Oncol 2008; 19: 1613-6.
64. Coxon A, Bush T, Saffran D, et al. Broad antitumor activity in breast cancer xenografts by motesanib, a highly selective, oral inhibitor of ascular endothelial growth factor, platelet-derived growth factor, and Kit receptors. Clin Cancer Res 2009; 15: 110-8.
65. Silva BV, Ribeiro NM, Vargas MD, et al. Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles. Dalton Trans 2010; 39: 7338-44.
66. Wang TC, Wei JZ, Guo CS, Zhang HB, Fan HX. Design, synthesis and anti-proliferative studies of a novel series of indirubin derivatives. Chin Chem Lett 2010; 21: 1407-10.
67. Kawakita Y, Banno H, Ohashi T, et al. Design and synthesis of pyrrolo[3,2-d]pyrimidine human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) dual inhibitors: exploration of novel back-pocket binders. J Med Chem 2012; 55: 3975-91.
68. Feldman ME, Shokat KM. In: Phosphoinositide 3-kinase in Health and Disease. Current Topics in Microbiology and Immunology. Rommel C, Vanhaesebroeck B, Vogt PK, Eds. Berlin-Heidelberg: Springer-Verlag 2010; Vol. 2: pp 241-62.
69. Zhang N, Ayral-Kaloustian S, Anderson JT, et al. 5- Ureidobenzofuranone indoles as potent and efficacious inhibitors of PI3 kinase-α and mTOR for the treatment of breast cancer. Bioorg Med Chem Lett 2010; 20: 3526-9.
70. Rawson TE, Rüth M, Blackwood E, et al. A pentacyclic aurora kinase inhibitor (AKI-001) with high in vivo potency and oral bioavailability. J Med Chem 2008; 51: 4465-75.
71. Craig S, Gao L, Lee I, Gray T, Berdis AJ. Gold-containing indoles as anticancer agents that potentiate the cytotoxic effects of ionizing radiation. J Med Chem 2012; 55: 2437-51.
72. Choi S-J, Lee J-E, Jeong S-Y, et al. 5,5'-Substituted indirubin-3'- oxime derivatives as potent cyclin-dependent kinase inhibitors with anticancer activity. J Med Chem 2010; 53: 3696-706.
73. Kassis P, Brzeszcz J, Bénéteau V, et al. Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5-(phenyl) pyridine or pyrazine V-shaped molecules as kinase inhibitors and cytotoxic agents. Eur J Med Chem 2011; 46: 5416-34.
74. Giraud F, Alves G, Debiton E, et al. Synthesis, protein kinase inhibitory potencies, and in vitro antiproliferative activites of meridianin derivatives. J Med Chem 2011; 54: 4474-89.
75. Gompel M, Leost M, Joffe EBDK, et al. Meridianins, a new family of protein kinase inhibitors isolated from the ascidian Aplidium meridianum. Bioorg Med Chem Lett 2004; 14: 1703-7.
76. Radwan MAA, El-Sherbiny M. Synthesis and antitumor activity of indolylpyrimidines: marine natural product meridianin D analogues. Bioorg Med Chem 2007; 15: 1206-11.
77. Kung AWC, Chu EYW, Xu L. Bazedoxifene: a new selective estrogen receptor modulator for the treatment of postmenopausal osteoporosis. Expert Opin Pharmacother 2009; 10: 1377-85.
78. Dykstra KD, Guo L, Birzin ET, et al. Estrogen receptor ligands. Part 16: 2-aryl indoles as highly subtype selective ligands for ERα. Bioorg Med Chem 2007; 17: 2322-8.
79. Lézé M-P, Palusczak A, Hartmann RW, Le Borgne M. Synthesis of 6- or 4-functionalized indoles via a reductive cyclization approach and evaluation as aromatase inhibitors. Bioorg Med Chem Lett 2008; 18: 4713-5.
80. Wu G, Liu J, Bi L, et al. Toward breast cancer resistance protein (BCRP) inhibitors: design, synthesis of a series of new simplified fumitremorgin analogues. Tetrahedron 2007; 63: 5510-28.
81. Jain HD, Zhang C, Zhou S, et al. Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein. Bioorg Med Chem 2008; 16: 4626-51.
82. Valdameri G, Gauthier C, Terreux R, et al. Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation oín both inhibition potency and cytotoxicity. J Med Chem 2012; 55: 3193-200.
83. Hall MDH, Brimacombe KR, Varonka MS, et al. Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein. J Med Chem 2011; 54: 5878-89.
84. Ocker M. Deacetylase inhibitors - focus on non-histone targets and effects. World J Biol Chem 2010; 1: 55-61.
85. Conte P, Campone M, Pronzato P, et al. Phase I trial of panobinostat (LBH589) in combination with trastuzumab in pretreated HER2-positive metastatic breast cancer (mBC): preliminary safety and tolerability results. J Clin Oncol 2009; 27: 15S-1081.
86. Mahboobi S, Sellmer A, Höcher H, et al. 2-Aroylindoles and 2- aroylbenzofurans with N-hydroxyacrylamide substructures as a novel series of rationally designed histone deacetylase inhibitors. J Med Chem 2007; 50: 4405-18.
87. Lai M-J, Huang H-L, Pan S-L, et al. Synthesis and biological evaluation of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo. J Med Chem 2012; 55: 3777-91.
88. Mohamed HA, Girgis NMR, Wilcken R, et al. Synthesis and molecular modelling of novel tetrahydro-β-carboline derivatives with phosphodiesterase 5 inhibitory and anticancer properties. J Med Chem 2011; 54: 495-509.
89. Go M-L, Leow JL, Gorla SK, Schüller AP, Wang M, Casey PJ. Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase. J Med Chem 2010; 53: 6838-50.
90. Donnelly AC, Mays JR, Burlison JA, et al. The design, synthesis, and evaluation of coumarin ring derivatives of the novobiocin scaffold that exhibit antiproliferative activity. J Org Chem 2008; 73: 8901-20.
91. Zhao H, Donnelly AC, Kusuma BR, et al. Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents. J Med Chem 2011; 54: 3839-53.
92. Yarim M, Koksal M, Schepmann D, Wünsch B. Synthesis and in vitro evaluation of novel indole-based sigma receptor ligands. Chem Biol Drug Des 2011; 78: 869-75.
93. McCarroll AJ, Bradshaw TD, Westwell AD, Matthews CS, Stevens MFG. Quinols as novel therapeutic agents. 7. Synthesis of antitumor 4-[1-(arylsulfonyl-1H-indol-2-yl)]-4-hydroxycyclohexa-2,5- dien-1-ones by Sonogashira reactions. J Med Chem 2007; 50: 1707-10.
94. Zhang W, Go M-L. Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity. Bioorg Med Chem 2009; 17: 2077-90.
95. Zhang D, Wang G, Zhao G, Xu W, Huo L. Synthesis and cytotoxic activity of novel 3-(1H-indol-3-yl)-1H-pyrazole-5-carbohydrazide derivatives. Eur J Med Chem 2011; 46: 5868-77.
96. Robinson MW, Overmeyer JH, Young AM, Erhardt PW, Maltese WA. Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death. J Med Chem 2012; 55: 1940-56.
97. Kumar R, Gupta L, Pal P, et al. Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents. Eur J Med Chem 2010; 45: 2265-76.
98. Penthala NR, Yerramreddy TR, Crooks PA. Synthesis and in vitro screening of novel N-benzyl aplysinopsin analogs as potential anticancer agents. Bioorg Med Chem Lett 2011; 21: 1411-3.
99. Zhang P, Sun X, Xu B, Bijian K, Wan S, Li G, Alaoui-Jamali M, Jiang T. Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives. Eur J Med Chem 2011; 46: 6089-97.
100. Zaima K, Hirata T, Hosoya T, et al. Biscarpamontamines A and B, an aspidosperma-iboga bisindole alkaloid and an aspidospermaaspidosperma bisindole alkaloid, from Tabernaemontana sphaerocarpa. J Nat Prod 2009; 72: 1686-90.
101. Robinson SJ, Morinaka BI, Amagata T, et al. New structures and bioactivity properties of jasplakinolide (jaspamide) analogues from marine spongues. J Med Chem 2010; 53: 1651-61.