2-Indolinone a versatile scaffold for treatment of cancer: A patent review (2008-2014)

Expert Opinion on Therapeutic Patents

Volumn 26, Issue 2, 2016, Pages 149-173

  Leoni, Alberto ^a   Locatelli, Alessandra ^a   Morigi, Rita ^a   Rambaldi, Mirella ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

2 indolinone; Histone deacetylase; Inhibitor; Mouse double minute 2; Oxindole; Polo like kinase; Tyrosine kinase inhibitors

Indexed keywords

ANTINEOPLASTIC AGENT; AURORA KINASE INHIBITOR; CHECK POINT KINASE 1 INHIBITOR; HISTONE DEACETYLASE INHIBITOR; INSULIN LIKE GROWTH FACTOR 1 RECEPTOR INHIBITOR; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; MOUSE DOUBLE MINUTE 2 ANTAGONIST; OXINDOLE; PHOSPHATASE MAGNESIUM DEPENDENT 1 INHIBITOR; PHOSPHOTRANSFERASE INHIBITOR; POLO LIKE KINASE INHIBITOR; PROTEIN MDM2; PROTEIN TYROSINE KINASE INHIBITOR; RIBOSOMAL S6 KINASE INHIBITOR; SOMATOMEDIN C RECEPTOR; TRANSGLUTAMINASE 2 INHIBITOR; UNCLASSIFIED DRUG; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR INHIBITOR; VASCULOTROPIN RECEPTOR; 2-OXINDOLE; INDOLE DERIVATIVE;

CANCER GROWTH; CANCER RESISTANCE; CANCER STEM CELL; CANCER THERAPY; CARCINOGENESIS; DRUG MECHANISM; DRUG POTENCY; HUMAN; IC50; MCF 7 CELL LINE; MULTIDRUG RESISTANCE; NEOPLASM; REVIEW; SIGNAL TRANSDUCTION; WESTERN BLOTTING; ANIMAL; CHEMISTRY; DRUG DESIGN; MEDICINAL CHEMISTRY; MOLECULARLY TARGETED THERAPY; NEOPLASMS; PATENT; PROCEDURES; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; INDOLES; MOLECULAR TARGETED THERAPY; NEOPLASMS; PATENTS AS TOPIC;

EID: 84957434091     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2016.1118059     Document Type: Review

References (131)

1. Wu Y-J. New indole-containing medicinal compounds. Berlin, Heidelberg: Springer; 2015. p. 1-29.
2. Garcia-Borreguero D, Grunstein R, Sridhar G, et al. A 52-week open-label study of the long-term safety of ropinirole in patients with restless leg syndrome. Sleep Med. 2007;8(7-8):742-752.
3. Greenberg WM, Citrome L. Ziprasidone for schizophrenia and bipolar disorder: a review of the clinical trials. CNS Drug Rev. 2007;13(2):137-177.
4. Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer. 2009;9 (1):28-39.
5. Prakash CR, Theivendren P, Raja S. Indolin-2-ones in clinical trials as potential kinase inhibitors: a review. Pharmacol Pharm. 2012;3(01):62.
6. Hilberg F, Roth GJ, Krssak M, , et al. BIBF 1120: triple angiokinase inhibitor with sustained receptor blockade and good antitumor efficacy. Cancer Res. 2008;68 (12):4774-4782.
7. Antoniu SA, Kolb MR. Intedanib, a triple kinase inhibitor of VEGFR, FGFR and PDGFR for the treatment of cancer and idiopathic pulmonary fibrosis. IDrugs. 2010;13(5):332-345.
8. Ikeda M, Shiina S, Nakachi K, et al. Phase I study on the safety, pharmacokinetic profile, and efficacy of the combination of TSU-68, an oral antiangiogenic agent, and S-1 in patients with advanced hepatocellular carcinoma. Invest New Drugs. 2014;32(5):928-936.
9. Trost BM, Brennan MK. Asymmetric syntheses of oxindole and indole spirocyclic alkaloid natural products. Synthesis. 2009;18:3003-3025.
10. Zhou F, Liu Y-L, Zhou J. Catalytic asymmetric synthesis of oxindoles bearing a tetrasubstituted stereocenter at the C-3 position. Adv Synth Catal. 2010;352(9):1381-1407.
11. Peddibhotla S. 3-Substituted-3-hydroxy-2-oxindole, an emerging new scaffold for drug discovery with potential anticancer and other biological activities. Curr Bioact Compd. 2015;5(1);20-38. [cited 2008 Nov 20]. Available from: http://www.eurekaselect.com/68899/article
12. Badillo JJ, Hanhan NV, Franz AK. Enantioselective synthesis of substituted oxindoles and spirooxindoles with applications in drug discovery. Curr Opin Drug Discov Devel. 2010;13(6):758-776.
13. Dalpozzo R, Bartoli G, Bencivenni G. Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones. Chem Soc Rev. 2012;41 (21):7247-7290.
14. Yu B, Yu DQ, Liu HM. Spirooxindoles: promising scaffolds for anticancer agents. Eur J Med Chem. 2015;97:673-698.
15. Chen HX, Sharon E. IGF-1R as an anti-cancer target-trials and tribulations. Chin J Cancer. 2013;32(5):242-252.
16. Singh P, Alex JM, Bast F. Insulin receptor (IR) and insulinlike growth factor receptor 1 (IGF-1R) signaling systems: novel treatment strategies for cancer. Med Oncol. 2014;31(1):805.
17. Pfizer Italia SRL 4-Arylpyrrole substituted 2-indoline derivatives active as protein kinase inhibitors. WO2008145398A1. 2008.
18. Sugen Inc. 5-Sulfonamide-substituted indolinone compounds as protein kinase inhibitors. US 7, 157, 577 B2. 2007.
19. Guan H, Liang C, Sun L et al. 3-(4-Amidopyrrol-2-ylmethlidene)-2-indolinone derivatives as protein kinase inhibitors. WO2002066463A1. 2002.
20. Boston Biomedical Inc. Compositions of kinase inhibitors and their use for treatment of cancer and other diseases related to kinases. WO2009033033. 2009.
21. Kreso A, Dick JE. Evolution of the cancer stem cell model. Cell Stem Cell. 2014;14(3):275-291.
22. Eaves CJ. Cancer stem cells here, there, everywhere?. Nature. 2008;456(7222):581-582.
23. Go ML, Ho HK, Zhang W Novel benzylidene-indolinone and their medical and diagnostic uses. WO2010044753A1. 2010.
24. Go ML, Han Kiat H, Xiao C Benzylidene-indolinone compounds and their medical use. US 8, 877, 946 B2. 2014.
25. Huang JJ, Chiang CC, Liu C et al. Indolinone compounds as kinase inhibitors. US 7, 897, 602 B2. 2011.
26. Zhang D, Xie G New indolinone protein kinase inhibitors. WO2012139019. 2012.
27. Boehringer Ingelheim Usa Corporation. 3-(Aminomethyliden) 2-indolinone derivatives and their use as cell proliferation inhibitors. US20090105216A1. 2009.
28. Boehringer Ingelheim Usa Corporation. Indoline derivatives and their use in treating disease-states such as cancer. US201001084747A1. 2010.
29. Boehringer Ingelheim Usa Corporation. Compounds. US 8, 853, 420 B2. 2014.
30. Annji Pharmaceutical Co., Ltd. Indolin-2-one derivatives as protein kinase inhibitors. US20130281451A1. 2013.
31. Janssen Pharmaceutica. Indolin-2-ones and aza-indolin-2-ones. WO2008155421A3. 2008.
32. Pauls HW, Forrest BT, Laufer R et al. Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer. WO2009079767A9. 2009.
33. Sampson PB, Liu Y, Le S-W et al. Kinase inhibitors and method of treating cancer with same. WO2010115279A1. 2010.
34. Eastwood PR, Gonzalez RJ, Giulio MV New substituted indolin-2-one derivatives and their use as p38 mitogenactivated kinase inhibitors. WO2009132774A8. 2009.
35. Hong P-C, Chen L-J, Llc D-U et al. Protein kinase inhibitors. WO2009085040 A1. 2009.
36. Li H, Liu X, Zhao Z, et al. Synthesis of indolinone derivative as RSK2 inhibitor and application. CN102688234A. 2012.
37. Lee SH, Song IH, Noh R, et al. Clinical outcomes of patients with advanced hepatocellular carcinoma treated with sorafenib: a retrospective study of routine clinical practice in multi-institutions. BMC Cancer. 2015;15:236.
38. Ko JJ, Xie W, Kroeger N, et al. International metastatic renal cell carcinoma database consortium model as a prognostic tool in patients with metastatic renal cell carcinoma previously treated with first-line targeted therapy: a population-based study. Lancet Oncology. 2015;16(3):293-300.
39. Hirth KP, McMahon G, Shawver LK, et al. Indolinone combinatorial libraries and related products and methods for the treatment of disease. WO1998007695A1. 1998.
40. Sun L, Tran N, Tang F, et al. Synthesis and biological evaluations of 3-substituted indolin-2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases. J Med Chem. 1998;41(14):2588-2603.
41. 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(23):6922-6924.
42. Cheung CHA, Sarvagalla S, Lee JY-C, et el. Aurora kinase inhibitor patents and agents in clinical testing: an update (2011-2013). Expert Opin Ther Patents. 2014;24(9):1021-1038.
43. Boehringer Ingelheim International Gmbh. Anticancer therapy. US20140194442A1. 2014.
44. Grunwald MR, Levis MJ. FLT3 inhibitors for acute myeloid leukemia: a review of their efficacy and mechanisms of resistance. Int J Hematol. 2013;97(6):683-694.
45. Liu L, Zhang CZ, Cai M, et al. Downregulation of Polo-like kinase 4 in hepatocellular carcinoma associates with poor prognosis. PLoS One. 2012;7(7):e41293.
46. Habedanck R, Stierhof YD, Wilkinson CJ, et al. The Polo kinase Plk4 functions in centriole duplication. Nat Cell Biol. 2005;7(11):1140-1146.
47. Mason JM, Lin DC, Wei X, et al. Functional characterization of CFI-400945, a Polo-like kinase 4 inhibitor, as a potential anticancer agent. Cancer Cell. 2014 Aug 11;26 (2):163-176.
48. Nagamatsu T, Yamasaki H. General syntheses of 1-alkyltoxoflavin and 8-alkylfervenulin derivatives of biological significance by the regioselective alkylation of reumycin derivatives and the rates of transalkylation from 1-alkyltoxoflavins into nucleophiles. J Chem Soc Perkin Trans. 2001;1(2):130-137.
49. Nagamatsu T, Yamasaki H, Hirota T, et al. Syntheses of 3-substituted 1-methyl-6-phenylpyrimido [5, 4-e]-1, 2, 4-triazine-5, 7(1H, 6H)-diones (6-phenyl analogs of toxoflavin) and their 4-oxides, and evaluation of antimicrobial activity of toxoflavins and their analogs. Chem Pharm Bull. 1993;41(2):362-368.
50. Cook ND. Scintillation proximity assay: a versatile highthroughput screening technology. Drug Discovery Today. 1996;1(7):287-294.
51. Rodems SM, Hamman BD, Lin C, et al. A FRET-based assay platform for ultra-high density drug screening of protein kinases and phosphatases. ASSAY Drug Dev Technol. 2002;1(1):9-19.
52. Heck RF, Nolley JP. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem. 1972;37(14):2320-2322.
53. Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev. 1995;95(7):2457-2483.
54. Chinchilla R, Najera C. The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem Rev. 2007;107(3):874-922.
55. Patil M, Pabla N, Dong Z. Checkpoint kinase 1 in DNA damage response and cell cycle regulation. Cell Mol Life Sci. 2013;70(21):4009-4021.
56. Carriere A, Ray H, Blenis J, et al. The RSK factors of activating the Ras/MAPK signaling cascade. Front Biosci. 2008;13:4258-4275.
57. Nguyen TL. Targeting RSK: an overview of small molecule inhibitors. Anticancer Agents Med Chem. 2008;8 (7):710-716.
58. Pontiki E, Hadjipavlou-Litina D. Histone deacetylase inhibitors (HDACIs). Structure-activity relationships: history and new QSAR perspectives. Med Res Rev. 2012;32(1):1-165.
59. Chen K, Xu L, Wiest O. Computational exploration of zinc binding groups for HDAC inhibition. J Org Chem. 2013;78 (10):5051-5055.
60. Gediya LK, Njar VCO. Promise and challenges in drug discovery and development of hybrid anticancer drugs. Exp Op Drug Disc. 2009;4(11):1099-1111.
61. Cai X, Qian C, Gould S Substituted 2-indolinone as ptk inhibitors containing a zinc binding moiety. US20080125478A1. 2008.
62. Spencer J Novel hybrid compounds. WO2012025726 A1. 2012.
63. Lu X-P, Li Z-B, Ning Z-Q 2-Indolinone derivatives as selective histone deacetylase inhibitors. US20090182029A1. 2009.
64. Lu X-P, Li Z-B, Ning Z-Q 2-Indolinone derivatives as selective histone deacetylase inhibitors. US7863315B2. 2011.
65. Hoffmann La Roche. Spiroindolinone derivatives. US20080114013A1. 2008.
66. Hoffmann La Roche. Spiroindolinone derivatives. US20080009486A1. 2008.
67. Hoffmann La Roche Oxindole derivatives as anticancer agents. WO2008034736A3. 2008.
68. Chu X-J, Ding Q, Jiang N, et al. Spiroindolinone pyrrolidines. US20110269809A1. 2011.
69. Chu X-J, Ding Q, Jiang N, et al Substituted spiro[3Hindole-3, 6(5H)-[1H]pyrrolo[1, 2c]imidazole-1, 2(1H, 2H)-diones. US20120071499A1. 2012.
70. Bartkovitz DJ, Chu X-J, Ding Q, et al. Spiroindolinone pyrrolidines. US20110130398A1. 2011.
71. Ascenta Therapeutics Inc., Sanofi, The Regents Of The University Of Michigan. Spiro-oxindole MDM2 antagonists. WO2012065022A2. 2012.
72. Wang S, Sun W, Aguilar A, et al. Spiro-oxindole mdm2 antagonists. WO2012155066A2. 2012.
73. The Institute of Cancer Research: Royal Cancer Hospital. Fused heterocyclic compounds and their use. WO2014030001A1. 2014.
74. Griffin J, Jin X, Khosla C, et al. 3-acylidene-2-oxoindole derivatives for inhibition of transglutaminase 2. WO2012078519A3. 2012.
75. Hall MD, Gottesman MM, Hellawell JL, et al. Compounds with mdr1-inverse activity. WO2009102433A2. 2009.
76. Brimacombe K, Fales HM, Gottesman MM, et al. Thiosemicarbazones with mdr1 -inverse activity. WO2012033601A1. 2012.
77. Toretsky JA, Aykut U, Lang MB, et al. Targeting of EWSFLI1 as anti-tumor Therapy. WO2008083326A2. 2008.
78. Halperin JA, Natarajan A, Aktas BH, et al. 3-3-Di-substituted-oxindoles as inhibitors of translation initiation. US20120077759A1. 2012.
79. Li Q, Lozano G. Molecular pathways: targeting Mdm2 and Mdm4 in cancer therapy. Clin Cancer Res. 2013;19(1):34-41.
80. Kamal A, Mohammed AA, Shaik TB. p53-Mdm2 inhibitors: patent review (2009-2010). Expert Opin Ther Patents. 2012;22(2):95-105.
81. Weber L. Patented inhibitors of p53-Mdm2 interaction (2006-2008). Expert Opin Ther Patents. 2010;20(2):179-191.
82. Khoo KH, Verma CS, Lane DP. Drugging the p53 pathway: understanding the route to clinical efficacy. Nat Rev Drug Discov. 2014;13(4):217.
83. Kussie PH, Gorina S, Marechal V, et al. Structure of the MDM2 oncoprotein bound to the p53 tumor suppressor transactivation domain. Science. 1996;274 (5289):948-953.
84. Wang S, Qin D, Chen J, et al. Indole inhibitors of MDM2 and the uses thereof. US7737174B2. 2007.
85. Wang S, Ding K, Lu Y, et al. Small molecule inhibitors of MDM2 and the uses thereof. US7759383B2. 2006.
86. Chen C, Li XD, Schreiber SL. Catalytic asymmetric 3+2 cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis. J Am Chem Soc. 2003;125 (34):10174-10175.
87. Alemparte C, Blay G, Jorgensen KA. A convenient procedure for the catalytic asymmetric 1, 3-dipolar cycloaddition of azomethine ylides and alkenes. Org Lett. 2005;7 (21):4569-4572.
88. Ding K, Lu Y, Nikolovska-Coleska Z, et al. Structure-based design of spiro-oxindoles as potent, specific small-molecule inhibitors of the MDM2-p53 interaction. J Med Chem. 2006;49(12):3432-3435.
89. Onishi T, Sebahar PR, Williams RM. Concise, asymmetric total synthesis of spirotryprostatin A. Tetrahedron. 2004;60(42):9503-9515.
90. Shangary S, Qin D, McEachern D, et al. Temporal activation of p53 by a specific MDM2 inhibitor is selectively toxic to tumors and leads to complete tumor growth inhibition. Proc Natl Acad Sci U S A. 2008;105 (10):3933-3938.
91. Zhao Y, Bernard D, Wang S. Small molecule inhibitors of MDM2-p53 and MDMX-p53 interactions as new cancer therapeutics. BioDiscovery. 2015;8:4.
92. Ding K, Lu Y, Nikolovska-Coleska Z, et al. Structure-based design of potent non-peptide MDM2 inhibitors. J Am Chem Soc. 2005;127(29):10130-10131.
93. Yu S, Qin D, Shangary S, et al. Potent and orally active small-molecule inhibitors of the MDM2-p53 interaction. J Med Chem. 2009;52(24):7970-7973.
94. Garcia-Echeverria C, Chene P, Blommers MJJ, et al. Discovery of potent antagonists of the interaction between human double minute 2 and tumor suppressor p53. J Med Chem. 2000;43(17):3205-3208.
95. Lammers T, Lavi S. Role of type 2C protein phosphatases in growth regulation and in cellular stress signaling. Crit Rev Biochem Mol Biol. 2007;42(6):437-461.
96. Fujimoto H, Onishi N, Kato N, et al. Regulation of the antioncogenic Chk2 kinase by the oncogenic Wip1 phosphatase. Cell Death Differ. 2006;13(7):1170-1180.
97. Tan DSP, Lambros MBK, Rayter S, et al. PPM1D is a potential therapeutic target in ovarian clear cell carcinomas. Clin Cancer Res. 2009;15(7):2269-2280.
98. Bulavin DV, Demidov ON, Saito S, et al. Amplification of PPM1D in human tumors abrogates p53 tumor-suppressor activity. Nat Genet. 2002;31(2):210-215.
99. Loukopoulos P, Shibata T, Katoh H, et al. Genome-wide array-based comparative genomic hybridization analysis of pancreatic adenocarcinoma: identification of genetic indicators that predict patient outcome. Cancer Sci. 2007;98(3):392-400.
100. Turkson J, Kim JS, Zhang SM, et al. Novel peptidomimetic inhibitors of signal transducer and activator of transcription 3 dimerization and biological activity. Mol Cancer Ther. 2004;3(3):261-269.
101. Hu X, Stern HM, Ge L, et al. Genetic alterations and oncogenic pathways associated with breast cancer subtypes. Mol Cancer Res. 2009;7(4):511-522.
102. Yu E, Ahn YS, Jang SJ, et al. Overexpression of the wip1 gene abrogates the p38 MAPK/p53/Wip1 pathway and silences p16 expression in human breast cancers. Breast Cancer Res Treat. 2007;101(3):269-278.
103. Siegel M, Khosla C. Transglutaminase 2 inhibitors and their therapeutic role in disease states. Pharmacol Ther. 2007;115(2):232-245.
104. Piper JL, Gray GM, Khosla C. Effect of prolyl endopeptidase on digestive-resistant gliadin peptides in vivo. J Pharmacol Exp Ther. 2004;311(1):213-219.
105. Shen DW, Cardarelli C, Hwang J, et al. Multiple drugresistant human kb carcinoma-cells independently selected for high-level resistance to colchicine, adriamycin, or vinblastine show changes in expression of specific proteins. J Biol Chem. 1986;261(17):7762-7770.
106. Ludwig JA, Szakacs G, Martin SE, et al. Selective toxicity of NSC73306 in MDR1-positive cells as a new strategy to circumvent multidrug resistance in cancer. Cancer Res. 2006;66(9):4808-4815.
107. Gottesman MM. Mechanisms of cancer drug resistance. Annu Rev Med. 2002;53:615-627.
108. Grohar PJ, Woldemichael GM, Griffin LB, et al. Identification of an inhibitor of the EWS-FLI1 oncogenic transcription factor by high-throughput screening. J Natl Cancer Inst. 2011;103(12):962-978.
109. Uren A, Tcherkasskaya O, Toretsky JA. Recombinant EWSFLI1 oncoprotein activates transcription. Biochemistry. 2004;43(42):13579-13589.
110. May WA, Lessnick SL, Braun BS, et al. The Ewing's-sarcoma EWS/FLI-1 fusion gene encodes a more potent transcriptional activator and is a more powerful transforming gene than FLI-1. Mol Cell Biol. 1993;13(12):7393-7398.
111. Grier HE, Krailo MD, Tarbell NJ, et al. Addition of ifosfamide and etoposide to standard chemotherapy for Ewing's sarcoma and primitive neuroectodermal tumor of bone. N Engl J Med. 2003;348(8):694-701.
112. Drescher DG, Ramakrishnan NA, Drescher MJ. Surface plasmon resonance (SPR) analysis of binding interactions of proteins in inner-ear sensory epithelia. Meth Mol Biol. 2009;493:323-343.
113. Pain VM. Initiation of protein synthesis in eukaryotic cells. Eur J Biochem. 1996;236(3):747-771.
114. Kozak M. An analysis of vertebrate messenger-RNA sequences -intimations of translational control. J Cell Biol. 1991;115(4):887-903.
115. Kozak M. A short leader sequence impairs the fidelity of initiation by eukaryotic ribosomes. Gene Expr. 1991;1 (2):111-115.
116. Natarajan A, Fan YH, Chen H, et al. 3, 3-Diaryl-1, 3-dihydroindol-2-ones as antiproliferatives mediated by translation initiation inhibition. J Med Chem. 2004;47(8):1882-1885.
117. Benzaquen LR, Brugnara C, Byers HR, et al. Clotrimazole inhibits cell proliferation in vitro and in vivo. Nat Med. 1995;1(7):534-540.
118. Watkins SJ, Norbury CJ. Translation initiation and its deregulation during tumorigenesis. Br J Cancer. 2002;86 (7):1023-1027.
119. Christensen MK, Bjoerkling F Substituted 3-(4-hydroxyphenyl)-indolin-2-one compounds. US20100227863A1. 2010.
120. Brugnara C, Halperin J, Fluckiger R, et al. Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation. US20040242563A1. 2004.
121. Butcher SP, Coulter TS, Felding J, et al. Diphenyl -indol-2-on compounds and their use in the treatment of cancer. WO2005097107A2. 2005.
122. Halperin JA, Natarajan A, Aktas H, et al. 3-3-di-substituted-oxindoles as inhibitors of translation initiation. WO2005080335 A1. 2005.
123. Ali MA, Ang CW, Ismail R, et al. Curcumin compounds containing indolizine and their preparations thereof. WO2012099451A1. 2012.
124. Ali MA, Ang CW, Ismail R, et al. Curcumin compounds and their preparations thereof. WO2012099454A1. 2012.
125. Prakash CR, Raja S. Indolinones as promising scaffold as kinase inhibitors: a review. Mini Rev Med Chem. 2012;12 (2):98-119.
126. Wang S, Sun W, Zhao Y, et al. SAR405838: an optimized inhibitor of MDM2-p53 interaction that induces complete and durable tumor regression. Cancer Res. 2014;74 (20):5855-5865.
127. Sampson PB, Liu Y, Forrest B, et al. The discovery of Polo-like kinase 4 inhibitors: identification of (1R, 2S)-2-(3-((E)-4-(((cis)-2, 6-dimethylmorpholino)methyl) styryl)-1H-indazol-6-yl)-5?-methoxyspiro[cyclopropane-1, 3?-indolin]-2?-one (CFI-400945) as a potent, orally active antitumor agent. J Med Chem. 2015;58(1):147-169.
128. Aparicio-Gallego G, Blanco M, Figueroa A, et al. New insights into molecular mechanisms of sunitinib-associated side effects. Mol Cancer Ther. 2011;10(12):2215-2223.
129. Furtmann N, Hu Y, Bajorath J. Comprehensive analysis of three-dimensional activity cliffs formed by kinase inhibitors with different binding modes and cliff mapping of structural analogues. J Med Chem. 2015;58 (1):252-264.
130. Hu Y, Furtmann N, Bajorath J. Current compound coverage of the kinome. J Med Chem. 2015;58(1):30-40.
131. Hu Y, Bajorath J. Exploring the scaffold universe of kinase inhibitors. J Med Chem. 2015;58(1):315-332.