Studies on cardiac ingredients of plants. XI. synthesis of new bufotoxin homologues utilizing scillarenin (the genuine aglycone of proscillaridin), and their biological activities

DOI: 10.1248/cpb.42.2256

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2256 - 2262 (1994)

Update date:2022-08-03

Topics:

Authors:

Tanase Tanase

Nagatsu Nagatsu

Murakami

Nagai Nagai

Ueda Ueda

Sakakibara

Ando Ando

Hotta Hotta

Takeya Takeya

Asano Asano

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.42.2256

New bufotoxin homologues (3) with various lengths of alkyl chain including longer ones thana suberoyl group at C-3 of the steroid nucleus were prepared from proscillaridin (1) via its genuine aglycone, scillarenin (2), in excellent yield. In the course of preparation, we established conditions for efficient enzymatic glycolysis of 1 to give 2 quantitatively. The pharmacological activities of the resulting bufotoxin homologues (3) were evaluated by measurement of the effect on smooth muscle using the mesenteric artery from spontaneously hypertensive rats, inhibitory: effect on Na⁺, K⁺-adenosine triphosphatase (ATPase) prepared from dog kidney, and positive inotropic effect (PIE) on isolated guinea-pig papillary muscle preparations; The bufotoxin homologues (3) showed only slight contraction of vascular muscle followed by a small-relaxation,in addition to the high Na⁺, K⁺-ATPase inhibitory activity and PIE comparable to those of clinically used ouabain, digoxin, and digitoxin. Those bufotoxin homologues (3) may be useful as cardiac agents with a minimal vascular contractile effect.

Full text of DOI:10.1248/cpb.42.2256

NII-Electronic Library Service

Products guided by the article

Product name:5-Isobutoxycarbonyloxy-5-oxo-pentanoic acid (3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Cas No:1060725-90-7

R&D Labs maybe for 1060725-90-7

Hangzhou Fandachem Co.,Ltd

Contact:+86-158-5814-5714

Address:No.9 YanAn Road,Hangzhou,Zhejiang,China
Engineering Research Center of Pesticide, Heilongjiang Province

Contact:+86-451-86609001

Address:No.74 of Xuefu Road, Nangang District,
uni source industries limited

Contact:86 21 3772 9386

Address:Rm.1803,Starry Bldg.1,1505 Meijiabang Road,Shanghai 201620 China
Zhejiang Tianyu Pharmaceutical Co., Ltd.

Contact:+86-576-84177669, 89189665,89189688,84168770

Address:Jiangkou Development Zone, Huangyan, Taizhou City, Zhejiang
Shantou Baokang Pharmaceutical Co., Ltd.

Contact:+86-754-88873487

Address:5/F B Block Huangshan Bldg Huangshan Rd Shantou

Relevant to this article

Synthetic approach toward antibiotic ezomycins. I. Synthesis of 5-amino-5-deoxyoctofuranose-(1,4) derivatives by Henry reaction and their stereochemistry

Doi:10.1246/bcsj.59.1753
(1986)
A Novel 3(2H)-Furanone-2(5H)-Furanone Rearrangement

Doi:10.1021/jo00379a040
(1987)
ATP-competitive inhibitors of the mammalian target of rapamycin: Design and synthesis of highly potent and selective pyrazolopyrimidines

Doi:10.1021/jm900851f
(2009)
Chemical and chemotaxonomic studies of pterophyten. LXIV. Chemical studies on the contents of Sceptridium ternatum var. ternatum

Doi:10.1248/cpb.34.3727
(1986)
1H,1H-Perfluoroalkylation of Enol Silyl Ethers with (1H,1H-Perfluoroalkyl)-phenyliodonium Triflates. A New Method for the Preparation of β- and δ-Trifluoromethyl Carbonyl Compounds and Their Higher Perfluoroalkyl Homologues

Doi:10.1246/bcsj.60.3823
(1987)
Synthesis study of 2′-O-(2-methoxyethyl)-purine derivatives

Doi:10.1080/15257770701528180
(2007)

Article Doi