The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

被引：96

作者：

Kerr, Daniel J.

Hamel, Ernest

Jung, M. Katherine

Flynn, Bernard L.

机构：

[1] Monash Univ, Fac Pharm, Dept Med Chem, Parkville, Vic 3052, Australia

[2] NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diagnosis, Ft Detrick, MD 21702 USA

[3] NCI, SAIC Frederick, NIH, Frederick, MD 21702 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 09期

关键词：

tubulin polymerisation inhibitor; chalcone; indanone; indenone;

D O I：

10.1016/j.bmc.2007.02.006

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3290 / 3298

页数：9

相关论文

共 50 条

[11] Synthesis, characterization and crystal structure of 4′-ethynylflavanone and its chalcone precursor [J].

Salinas-Ortega, Ismael ;

Ocayo, Fernanda ;

Santos, Juan C. ;

Trujillo, Alexander ;

Escobar, Carlos A. .

JOURNAL OF MOLECULAR STRUCTURE, 2017, 1128 :361-367

[12] Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity [J].

Kolundzija, Branka ;

Markovic, Violeta ;

Stanojkovic, Tatjana ;

Joksovic, Ljubinka ;

Matic, Ivana ;

Todorovic, Nina ;

Nikolic, Marijana ;

Joksovic, Milan D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (01) :65-71

[13] Chalcone based azacarboline analogues as novel antitubulin agents: Design, synthesis, biological evaluation and molecular modelling studies [J].

Sharma, Sahil ;

Kaur, Charanjit ;

Budhiraja, Abhishek ;

Nepali, Kunal ;

Gupta, Manish K. ;

Saxena, A. K. ;

Bedi, P. M. S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 :648-660

[14] Synthesis and biological evaluation of chalcone analogues as protective agents against cisplatin-induced cytotoxicity in kidney cells [J].

Lee, Dahae ;

Kim, Ki Hyun ;

Moon, Sung Won ;

Lee, Heesu ;

Kang, Ki Sung ;

Lee, Jae Wook .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (09) :1929-1932

[15] β-Lactam analogues of combretastatin A-4 prevent metabolic inactivation by glucuronidation in chemoresistant HT-29 colon cancer cells [J].

Malebari, Azizah M. ;

Greene, Lisa M. ;

Nathwani, Seema M. ;

Fayne, Darren ;

O'Boyle, Niamh M. ;

Wang, Shu ;

Twamley, Brendan ;

Zisterer, Daniela M. ;

Meegan, Mary J. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 130 :261-285

[16] Microwave assisted synthesis of chalcone and its polycyclic heterocyclic analogues as promising antibacterial agents: In vitro, in silico and DFT studies [J].

Khan, Salman A. ;

Asiri, Abdullah M. ;

Al-Ghamdi, Najat Saeed M. ;

Asad, Mohammad ;

Zayed, Mohie E. M. ;

Elroby, Shabaan A. K. ;

Aqlan, Faisal M. ;

Wani, Mohmmad Younus ;

Sharma, Kamlesh .

JOURNAL OF MOLECULAR STRUCTURE, 2019, 1190 :77-85

[17] Synthesis and Biological Activity Evaluation of Novel Chalcone Analogues Containing a Methylxanthine Moiety and Their N-Acyl Pyrazoline Derivatives [J].

Wang, Lei ;

Fan, Wenqi ;

Cui, Li ;

Yang, Na ;

Zhang, Xiao ;

Yu, Shujing ;

Li, Yonghong ;

Wang, Baolei .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2023, 71 (49) :19343-19356

[18] Synthesis of Renoprotective Chalcone Analogues That Protect Against Cisplatin-induced Cytotoxicity in LLC-PK1 Cells [J].

Yamabe, Noriko ;

Lee, Dahae ;

Lee, Heesu ;

Shin, Myung Sook ;

Hwang, Gwi Seo ;

Kang, Ki Sung ;

Lee, Jae Wook .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (11) :1882-1885

[19] Synthesis, crystal structure, in-silico ADMET, molecular docking and dynamics simulation studies of thiophene-chalcone analogues [J].

Nanjundaswamy, S. ;

Gurumallappa ;

Hema, M. K. ;

Karthik, C. S. ;

Rajabathar, Jothi Ramalingam ;

Arokiyaraj, Selvaraj ;

Lokanath, N. K. ;

Mallu, P. .

JOURNAL OF MOLECULAR STRUCTURE, 2022, 1247

[20] Novel fluorophenyl tethered thiazole and chalcone analogues as potential anti-tubercular agents: Design, synthesis, biological and in silico evaluations [J].

Kushwaha, Babita ;

Kushwaha, Narva Deshwar ;

Priya, Manisha ;

Chandrasekaran, Balakumar ;

Obakachi, Vincent A. ;

Chauhan, Ruchika ;

Kidwai, Saqib ;

Singh, Ramandeep ;

Ganai, Ab Majeed ;

Karpoormath, Rajshekhar .

JOURNAL OF MOLECULAR STRUCTURE, 2023, 1276

← 1 2 3 4 5 →