Progress in cis-Restricted Derivations of Combretastatin A-4

Abstract

Abstract:

Combretastatin A-4 (CA4) is an important new generation vascular disrupting agent (VDA) from plant. The cis-stilbene configuration of which plays a crucial role on antitumor and anti-vascular activities. The ring formation in ethylene moiety has been considered to be the main idea for structure modification of CA4. The recent progress in cis-restricted derivations of CA4 representing by three, five, six-membered ring formation as well as skeleton extension has been reviewed.

Key words: combretastatin A-4, SAR, cis-restriction, derivation, VDA

XIAO Chun-Fen, SUN Hong-Yi, WEI Wen, DU Jian-Li, ZOU Yong. Progress in cis-Restricted Derivations of Combretastatin A-4[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2011, 23(1): 169-185.

References

1 Pettit GR, et al.Isolation and structure of the strong cell growth and tubulin inhibitor Combretastatin A-4.Experientia,1989,45:209-211.
2 Lin CM,et al.Antimitotic natural products combretastatin A-4 and combretastatin A-2:studies on the mechanism of their inhibition of the binding of colchicine to tubulin.Biochemistry,1989,28:6984-6991.
3 Hori K,et al.Antitumor effects due to irreversible stoppage of tumor tissue blood flow:evaluation of a novel combretastatin A-4 derivative,AC7700.Jpn J Cancer Res,1999,90:1026-1038.
4 Nihei Y,et al.A novel combretastatin A-4 derivative, AC-7700,shows marked antitumor activity against advanced solid tumors and orthotopically transplanted tumors.Jpn J Cancer Res,1999,90:1016-1025.
5 Tozer GM,et al.Combretastatin A-4 phosphate as a tumor vascular-targeting agent:early effects in tumors and normal tissues. Cancer Res,1999,59:1626-1634.
6 Pettit GR,Rhodes MR.Antineoplastic agents 389.new syntheses of the combretastatin A-4 prodrug. Anti-Cancer Drug Design,1998,13:183-191.
7 Woods JA,et al.The interaction with tubulin of series of stilbenes based on combretastatin A-4.Br J Cancer,1995,71:705-711.
8 Hadfield JA,et al.Synthesis and evaluation of double bond substituted combretastatins.Eur J Med Chem, 2005,40:529-541.
9 Shirai R,et al.Asymmetric synthesis of anti-mitotic combretadioxolane with potent anti-tumor activity against multi-drug resistant cells.Bioorg Med Chem Lett,1998,8:1997-2000.
10 Nam NH,et al.Combretoxazolones: synthesis, cytotoxicity and antitumor activity.Bioorg & Med Chem Lett,2001,11:3073-3076.
11 Flynn BL,et al.The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4.Bioorg Med Chem Lett,2001,11:2341-2343.
12 Nam NH,et al.Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues. Bioorg Med Chem Lett,2002,12:1955-1958.
13 Wang L,et al.Potent, orally active heterocycle-based combretastatin a-4 analogues:synthesis, structure-activity relationship,pharmacokinetics, and in vivo antitumor activity evaluation.J Med Chem, 2002,45:1697-1711.
14 Kim Y,et al. Synthesis and cytotoxicity of 3,4-diaryl-2- (5H)-furanones.Bioorg & Med Chem Lett,2002, 12:719-722.
15 Kaffy J,et al.1,3-Dipolar cycloaddition route to novel isoxazole-type derivatives related to combretastatin A-4.Tetrahedron Lett,2004,45:3359-3362.
16 Kaffy J,et al.Isoxazole-type derivatives related to combretastatin A-4,synthesis and biological evaluation. Bioorg & Med Chem,2006,14:4067–4077.
17 Tron GC,et al.Synthesis and cytotoxic evaluation of combretafurazans.J Med Chem,2005, 48:3260-3268.
18 Simoni D,et al.Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines.J Med Chem,2005,48:723-736.
19 Banwell MG,et al.4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatinA-4/lamellarin T hybrids: Synthesis and evaluation as anti-mitotic and cytotoxic agents.Bioorg & Med Chem,2006,14:4627-4638.
20 Peifer C,et al.Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors.J Med Chem,2006,49:1271-1281.
21 Wu MJ,et al.Synthesis and activity of Combretastatin A-4 analogues:1,2,3-thiadiazoles as potent antitumor agents.Bioorg Med Chem Lett,2007,17:869-873.
22 Johnson M,et al.Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4. Bioorg Med Chem Lett,2007,17:5897–5901.
23 Sun CM,et al.Synthesis and cytotoxic activities of 4,5-diarylisoxazoles. Bioorg Med Chem Lett,2007, 17:1078–1081. 24 Odlo K,et al.1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis,molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin.Bioorg Med Chem,2008,16:4829-4838.
25 Xue N,et al.Synthesis and biological evaluation of imidazol-2-one derivatives as potential antitumor agents.Bioorg Med Chem,2008,16:2550-2557.
26 Flynn BL,et al.One-pot synthesis of benzobfuran and indole inhibitors of tubulin polymerization.J Med Chem.2002,45:2670-2673.
27 Brown ML,et al.Comparative molecular field analysis of colchicine inhibition and tubulin polymerization for combretastatins binding to the colchicine binding site on tubulin.Bioorg Med Chem, 2000,8:1433-1441.
28 Lin CM,et al.Interaction of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin:a structure-activity study.Mol Pharm,1988,34,200-208.
29 Quintin J,et al.Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins. Tetrahedron,2006,62:4038-4051.
30 Lee L,et al.1, 2, 3, 4-Tetrahydro-2-thioxopyrimidine analouges of combretastatin-A4.Eur J Med Chem, 2008,43:2011-2015.
31 Lawrence NJ,et al.The synthesis of indanones related to combretastatin A-4 via microwave-assisted Nazarov cyclization of chalcones.Tetrahedron Lett,2006,47:1637-1640.
32 Kerr DJ,et al.The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4. Bioorg Med Chem,2007,15:3290–3298.
33 Nancy T,et al.Synthesis and biological evaluation of new disubstituted analogues of 6-methoxy-3-(3',4',5'-trimethoxybenzoyl)-1H-indole (BPR0L075),as potential antivascular agents.Bioorg Med Chem,2008,16:7494–7503.
34 Sriram M,et al.Design, synthesis and biological evaluation of dihydronaphthalene and benzosuberene analogs of the combretastatins as inhibitors of tubulin polymerization in cancer chemotherapy.Bioorg Med Chem,2008,16:8161–8171.

[1]	LUO Xu-dong, LI Xin-rong, LI Cheng-yi, QI Peng, LIANG Ting-ting, FENG Xiao-li, JIA Miao-ting, WANG Yan. Comparative study on rubbed and unrubbed Hedysari Radix based on multi-component determination [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2024, 36(7): 1215-1225.
[2]	CHEN Xiang-li, ZHANG Hui-min, ZHANG Zi-jia. Study on the spectrum-effect relationship between UPLC fingerprint and alkaline phosphatase activity in osteosarcoma MG63 cell of Drynariae Rhizoma [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2024, 36(2): 293-302.
[3]	WANG Yan, QIANG Zheng-ze, JIA Miao-ting, WEI Xiao-cheng, WANG Ming-wei, LI Shuo, LI Cheng-yi. Comparative study on rubbed and unrubbed Hedysari Radix samples based on trait-micro-fingerprinting [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2023, 35(8): 1402-1415.
[4]	SHAO Jin-hua, LIU Yi-lin, LYU Jing-kun, CHEN Xiao-ming. Alkaloids from leaves of Piper sarmentosum [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2023, 35(2): 231-235.
[5]	SHAO Jin-hua, XU Tuo, LYU Jing-kun, CHEN Xiao-ming. A new amide alkaloid from the root of Piper sarmentosum [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2023, 35(12): 2082-2087.
[6]	WANG Yan, QIANG Zheng-ze, LI Cheng-yi, JIA Miao-ting, WEI Xiao-cheng, WANG Ming-wei, LI Shuo. Correlation between color and carotenoids in Hedysari Radix [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2023, 35(10): 1679-1698.
[7]	ZHANG Yu, ZHANG Hong, LI Ning, CHEN Juan. Research progress on chemical constituents and pharmacological effects of Asari Radix et Rhizoma and predictive analysis of its quality marker [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2023, 35(10): 1794-1807.
[8]	LI Hui-yuan, YUE Jing-yi, WANG Ju-tao, CAI Bai-xiang. Study on secondary metabolites of plant endophytic fungus Fusarium guttiforme [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(7): 1143-1147.
[9]	WANG Jiao-jiao, YUAN Ping-chuan, XU Han-chi, CHEN Ying, ZHANG Si-jia, TIAN Meng-yun, YU Zi-qi, LIU Chun-yan. Mechanism of apoptosis induced by exopolysaccharides from Fusarium graminearum on SGC-7901 cells#br# #br# [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(7): 1204-1212.
[10]	MIAO Yong-mei, HAN Shuo, MIAO Cui-ping, ZHANG Wei, XU Rong-hua. Isolation,identification and fermentation conditions optimization of endophytes from Bulbophyllum sp.and its inhibitory effect on Fusarium oxysporum f.sp.vasinfectum [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(4): 656-664.
[11]	LIU Jia-li, REN Wei, YANG Si-jin, TANG Run, MAO Lin-shen, SHUI Pi-xian. Study on the effective ingredients and potential mechanism of Sargentodoxa cuneata in the treatment of cerebral infarction based on UPLC-HR-MS and network pharmacology [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(3): 436-447.
[12]	LIANG Wei-zhong, XIAO Yi-wen, ZHANG Wen-hui, WANG Ya, GAO Bo-liang, ZHU Du. Isolation of secondary metabolites and antimicrobial activity of endophytic fungus Sarocladium oryzae L99 [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(增刊1): 35-42.
[13]	DENG Shuo-qiu, TIAN Ya, CHEN Li-na, SHEN Shuo, YANG Yuan-min, ZHANG Yu, QU Shui-qing, ZHENG Zhong-yuan, LIU Hui, WANG Xi, LI Hong-mei, LI Yu-jie. Study on the mechanism of artesunatum-puerarin combination in interventing COVID-19 cardiovascular complications based on network pharmacology [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(增刊1): 70-80.
[14]	FAN Chen-yang, MA Xuan, JI Zhi-hong, LI Ke-ao, ZHOU Wen-ting. Study on network pharmacology and molecular docking of Hanchuanzupa granules in treating COVID-19 [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(增刊1): 93-99.
[15]	LI Xiao-jie, LI Feng-ming, XU Liang-xiong, LI Ling , PENG Yong-hong. Antifungal secondary metabolites of endophytic Fusarium sp. HU0174 from Celtis sinensis [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(6): 943-950.