One pot synthesis and anticancer activity of dimeric phloroglucinols

被引：39

作者：

Chauthe, Siddheshwar K. ^{[1
]}

Bharate, Sandip B. ^{[1
]}

Periyasamy, Giridharan ^{[2
]}

Khanna, Amit ^{[2
]}

Bhutani, Kamlesh K. ^{[1
]}

Mishra, Prabhu D. ^{[2
]}

Singh, Inder P. ^{[1
]}

机构：

[1] NIPER, Dept Nat Prod, Sas Nagar 160062, Punjab, India

[2] Piramal Life Sci Ltd, Bombay 400063, Maharashtra, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 06期

关键词：

Phloroglucinol; Anticancer; Dimeric; Cytotoxic; 2,4-Diacetyl phloroglucinol; CYTOTOXIC CONSTITUENTS; BIOMIMETIC SYNTHESIS; ACYLPHLOROGLUCINOL DERIVATIVES; PERICARPS; ANTIMALARIAL; EUGLOBALS; REAGENT; PHENOLS;

D O I：

10.1016/j.bmcl.2012.01.089

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of dimeric phloroglucinol compounds were synthesized in a single step using commercially available phloroglucinol and methanesulfonic acid. Based on the reported anticancer activity of plant derived dimeric phloroglucinols, these synthesized compounds were evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Several compounds demonstrated in vitro cytotoxic effects across a wide array of tumor cell types. The compound 29 with pyridin-3-yl group on linker methylene and two diisovaleryl phloroglucinol moieties was found to be the most active in all the five cancer cell lines having a low IC50 of 5.5 mu M in colon cancer cell lines (HCT116). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2251 / 2256

页数：6

共 21 条

[1]

ANJANEYULU ASR, 1987, INDIAN J CHEM B, V26, P823

[2]

ARISAWA M, 1990, CHEM PHARM BULL, V38, P1624, DOI 10.1248/cpb.38.1624

[3] INHIBITION OF TUMOR-PROMOTER-ENHANCED H-3 CHOLINE INCORPORATION INTO CELLULAR PHOSPHOLIPIDS BY PHLOROGLUCINOL DERIVATIVES FROM MALLOTUS-JAPONICUS [J].

ARISAWA, M ;

FUJITA, A ;

MORITA, N ;

OKUYAMA, T ;

NISHINO, H .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (05) :1409-1412

[4] STUDIES ON CYTOTOXIC CONSTITUENTS IN PERICARPS OF MALLOTUS-JAPONICUS .2. [J].

ARISAWA, M ;

FUJITA, A ;

SAGA, M ;

HAYASHI, T ;

MORITA, N ;

KAWANO, N ;

KOSHIMURA, S .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (02) :298-302

[5] STUDIES ON CYTO-TOXIC CONSTITUENTS IN PERICARPS OF MALLOTUS-JAPONICUS .1. [J].

ARISAWA, M ;

FUJITA, A ;

SUZUKI, R ;

HAYASHI, T ;

MORITA, N ;

KAWANO, N ;

KOSHIMURA, S .

JOURNAL OF NATURAL PRODUCTS, 1985, 48 (03) :455-459

[6] CYTOTOXIC AND ANTITUMOR CONSTITUENTS IN PERICARPS OF MALLOTUS-JAPONICUS [J].

ARISAWA, M ;

FUJITA, A ;

MORITA, N ;

KOSHIMURA, S .

PLANTA MEDICA, 1990, 56 (04) :377-379

[7]

ARISAWA M, 1990, CHEM PHARM BULL, V38, P698, DOI 10.1248/cpb.38.698

[8] S-Euglobals:: Biomimetic synthesis, antileishmanial, antimalarial, and antimicrobial activities [J].

Bharate, Sandip B. ;

Khan, Shabana I. ;

Tekwani, Babu L. ;

Jacob, Melissa ;

Khan, Ikhlas A. ;

Singh, Inder Pal .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (03) :1328-1336

[9] Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols [J].

Bharate, Sandip B. ;

Khan, Shabana I. ;

Yunus, Nafees A. M. ;

Chauthe, Siddheshwar K. ;

Jacob, Melissa R. ;

Tekwani, Babu L. ;

Khan, Ikhlas A. ;

Singh, Inder Pal .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (01) :87-96

[10] Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues [J].

Bharate, SB ;

Bhutani, KK ;

Khan, SI ;

Tekwani, BL ;

Jacob, MR ;

Khan, IA ;

Singh, IP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (06) :1750-1760

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