Synthesis and structure–activity relationships study of novel anti-tumor carbamate anhydrovinblastine analogues

Shao, Yong; Ding, Hong; Tang, Weidong; Lou, Liguang; Hu, Lihong

doi:10.1016/j.bmc.2007.05.045

Cited by 22 publications

(10 citation statements)

References 19 publications

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“…On the other hand, oxidation of 20 (as a mixture with 21 ) did not proceed beyond the aldehyde stage, thus weakening the prospects of synthesizing the corresponding alkylcarboxamide via the carboxylic acid route. Sequential treatment of 24 and 25 with carbonyldiimidazole and ethylamine afforded the 5′- O ethylcarbamate derivatives 26 and 27 , [19] which were deprotected with NH 4 F in warm methanol to give the desired 5′- O -ethylcarbamate apionucleosides 13 and 14 in excellent yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of N6-substituted apioadenosines as potential adenosine A3 receptor modulators

Toti

Moss

Paoletta

et al. 2014

Bioorganic & Medicinal Chemistry

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Adenosine receptors (ARs) trigger signal transduction pathways inside the cell when activated by extracellular adenosine. Selective modulation of the A3AR subtype may be beneficial in controlling diseases such as colorectal cancer and rheumatoid arthritis. Here, we report the synthesis and evaluation of β-D-apio-D-furano- and α-D-apio-L-furanoadenosines and derivatives thereof. Introduction of a 2-methoxy-5-chlorobenzyl group at N6 of β-D-apio-D-furanoadenosine afforded an A3AR antagonist (10c, Ki = 0.98 μM), while a similar modification of an α-D-apio-L-furanoadenosine gave rise to a partial agonist (11c, Ki = 3.07 μM). The structural basis for this difference was examined by docking to an A3AR model; the antagonist lacked a crucial interaction with Thr94.

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Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of N6-substituted apioadenosines as potential adenosine A3 receptor modulators

Toti

Moss

Paoletta

et al. 2014

Bioorganic & Medicinal Chemistry

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“…The key intermediate amine 4 was prepared easily in four steps from vindoline according to a previously reported procedure. 14 N-Acylation of amine 4 was obtained with sodium hydride and complex BtCOR, which was prepared using a different acyl chloride or acid anhydride reacted with benzotriazole. Subsequently, the N-acylated compounds were further acetylated at C-4 OH to afford the amide vindoline derivatives 5a-24a, which, upon coupling with catharanthine (3) by the modified Polonovski-Potier reaction, produced targeted amide anhydrovinblastine analogues (5b-24b).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structure−Activity Relationship Studies of Cytotoxic Anhydrovinblastine Amide Derivatives

et al. 2009

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A series of 3-demethoxycarbonyl-3-amide methyl anhydrovinblastine derivatives (5b-24b) was designed, synthesized, and evaluated for their proliferation inhibition activities against two tumor cell lines (A549 and HeLa). Most of the amide anhydrovinblastine derivatives exhibited potent cytotoxicity, with the size of the introduced substituents being the foremost factor in determining the resultant cytotoxic activity. Test results in vivo against sarcoma 180 of three potent compounds (6b, 12b, and 24b) indicated that the introduction of an amide group at the 22-position of anhydrovinblastine (1e) improved both potency and toxicity.

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“…In non-small cell lung cancer, melanoma, breast cancer, colon cancer, and P388 and L1210 leukemia, nitro derivatives of amino vinblastine have anticancer action. Shao et al [ 117 ] observed human non-small lung cancer and human cervix epithelial adenocarcinoma cell lines treated with carbamate derivatives of vinblastine displayed anticancer activity. Similarly, the growth of HeLa cells was inhibited by amide substituted anhydrous vinblastine derivatives [ 116 ].…”

Section: Anticancer/cytotoxic Potential Of Alkaloids: Pharmacological...mentioning

confidence: 99%

Anticancer potential of alkaloids: a key emphasis to colchicine, vinblastine, vincristine, vindesine, vinorelbine and vincamine

et al. 2022

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Cancer, one of the leading illnesses, accounts for about 10 million deaths worldwide. The treatment of cancer includes surgery, chemotherapy, radiation therapy, and drug therapy, along with others, which not only put a tremendous economic effect on patients but also develop drug resistance in patients with time. A significant number of cancer cases can be prevented/treated by implementing evidence-based preventive strategies. Plant-based drugs have evolved as promising preventive chemo options both in developing and developed nations. The secondary plant metabolites such as alkaloids have proven efficacy and acceptability for cancer treatment. Apropos, this review deals with a spectrum of promising alkaloids such as colchicine, vinblastine, vincristine, vindesine, vinorelbine, and vincamine within different domains of comprehensive information on these molecules such as their medical applications (contemporary/traditional), mechanism of antitumor action, and potential scale-up biotechnological studies on an in-vitro scale. The comprehensive information provided in the review will be a valuable resource to develop an effective, affordable, and cost effective cancer management program using these alkaloids.

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Synthesis and structure–activity relationships study of novel anti-tumor carbamate anhydrovinblastine analogues

Cited by 22 publications

References 19 publications

Synthesis and evaluation of N6-substituted apioadenosines as potential adenosine A3 receptor modulators

Synthesis and evaluation of N6-substituted apioadenosines as potential adenosine A3 receptor modulators

Synthesis and Structure−Activity Relationship Studies of Cytotoxic Anhydrovinblastine Amide Derivatives

Anticancer potential of alkaloids: a key emphasis to colchicine, vinblastine, vincristine, vindesine, vinorelbine and vincamine

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