Antitumor Agents. 192. Antitubulin Effect and Cytotoxicity of C(7)-Oxygenated Allocolchicinoids

Guan, Jian; Zhu, Xiao Kang; Brossi, Arnold; Tachibana, Yoshihisa; Bastow, Kenneth F.; Verdier-Pinard, Pascal; Hamel, Ernest; McPhail, Andrew T.; Lee, Kuo Hsiung̀

doi:10.1135/cccc19990217

Cited by 21 publications

(13 citation statements)

References 15 publications

(21 reference statements)

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“…6 The1 H NMR matched that reported by Lee and coworkers. IR (CCl 4 ) 3006 (w), 2961 (m), 2932 (s), 2861 (w), 2832 (m), 1686 (s), 1605 (s), 1489 (s), 1408 (s), 1104 (s); 13 C NMR (N-Acetylcolchinol methyl ether (2).…”

supporting

confidence: 85%

“…Column chromatography (TLC R f = 0.27 40% acetone/pentane) yielded 78.7 mg (61%) of a white solid mp 203-204 °C (lit. 204-205 °C) 6. In CDCl 3 , two atropisomers were observed in approximately a 5:2 ratio, however, only one J=8.4, 1H);13 C NMR (DMSO) δ 23.5, 31.0, 49.0, 55.8, 56.7, 61.4, 61.4, 80.1, 108.9, 110.3, 111.6, 125.2, 127.0, 131.4, 135.6, 141.4, 142.7, 151.2, 153.0, 159.2, 169.2; LRMS (EI + ) m/z 372 (M + + H, 100), 314 (10), 313 (40); HRMS (EI + , M + + H) m/z calcd for C 21 H 25 NO 5 372.1811, found 372.1812.…”

mentioning

confidence: 99%

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Application of Aryl Siloxane Cross‐Coupling to the Synthesis of Allocolchicinoids.

Seganish

DeShong

2006

ChemInform

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supporting

confidence: 85%

mentioning

confidence: 99%

Application of Aryl Siloxane Cross‐Coupling to the Synthesis of Allocolchicinoids.

Seganish

DeShong

2006

ChemInform

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“…27 Allocolchinoids ( 55 – 57 ), with a six-membered rather than seven-membered C-ring, also showed significant antitubulin effects and cytotoxicity, even against three drug-resistant KB cell lines compared with the parental KB cell line (Table 2). 28…”

Section: Antitumor Agentsmentioning

confidence: 99%

Discovery and Development of Natural Product-Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach

2010

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Medicinal plants have long been an excellent source of pharmaceutical agents. Accordingly, the long term objectives of the author's research program are to discover and design new chemotherapeutic agents based on plant-derived compound leads by using a medicinal chemistry approach, which is a combination of chemistry and biology. Different examples of promising bioactive natural products and their synthetic analogs, including sesquiterpene lactones, quassinoids, naphthoquinones, phenylquinolones, dithiophenediones, neo-tanshinlactone, tylophorine, suksdorfin, DCK, and DCP, will be presented with respect to their discovery and preclinical development as potential clinical trial candidates. Research approaches include bioactivity- or mechanism of action-directed isolation and characterization of active compounds, rational drug design-based modification and analog synthesis, as well as structure-activity relationship and mechanism of action studies. Current clinical trials agents discovered by the Natural Products Research Laboratories, University of North Carolina, include bevirimat (dimethyl succinyl betulinic acid), which is now in Phase IIb trials for treating AIDS. Bevirimat is also the first in a new class of HIV drug candidates called “maturation inhibitors”. In addition, an etoposide analog, GL-331, progressed to anticancer Phase II clinical trials, and the curcumin analog JC-9 is in Phase II clinical trials for treating acne and in development for trials against prostate cancer. The discovery and development of these clinical trials candidates will also be discussed.

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“…( 7 ), and have been suggested to be catabolic metabolites of colchicines [ 117 , 118 ]. They usually retain the colchicine-type alkaloids ability to bind to tubulin but are less toxic, which has yielded some interest as potential antitumor drugs [ 34 , 119 ].…”

Section: Alkaloid Diversitymentioning

confidence: 99%

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

Larsson¹,

Rønsted

2013

CTMC

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The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways.

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Antitumor Agents. 192. Antitubulin Effect and Cytotoxicity of C(7)-Oxygenated Allocolchicinoids

Cited by 21 publications

References 15 publications

Application of Aryl Siloxane Cross‐Coupling to the Synthesis of Allocolchicinoids.

Application of Aryl Siloxane Cross‐Coupling to the Synthesis of Allocolchicinoids.

Discovery and Development of Natural Product-Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

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