Simple antitumor model compounds for cross-conjugated cyclopentenone prostaglandins

被引：11

作者：

Vostrikov, Nikolay S. ^{[1
]}

Spirikhin, Leonid V. ^{[1
]}

Lobov, Alexander N. ^{[1
]}

Gimazetdinov, Airat M. ^{[1
]}

Zileeva, Zulfiya R. ^{[2
]}

Vakhitova, Yulia V. ^{[2
]}

Macaev, Zainutdin R. ^{[1
]}

Pivnitsky, Kashmir K. ^{[3
]}

Miftakhov, Mansur S. ^{[1
]}

机构：

[1] Russian Acad Sci, Ufa Inst Chem, Ufa 450054, Russia

[2] Russian Acad Sci, Inst Biochem & Genet, Ufa 450054, Russia

[3] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

MENDELEEV COMMUNICATIONS | 2019年 / 29卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

15-DEOXY-DELTA(12,14)-PROSTAGLANDIN J(2); 15D-PGJ(2);

D O I：

10.1016/j.mencom.2019.07.003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unstable methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate, having a ring moiety of J-type prostaglandins (PGJs) and similar cytotoxicity, reacts with EtSH and other thiols with formation of mono- and bis-adducts, which have been further converted by oxidation with mCPBA into corresponding stable mono-sulfones possessing cytotoxic effect most probably due to in vivo regeneration of the starting dienone. Thus, the derived sulfones can be used as transport forms for original dienone as a pharmacologically important moiety of Delta(12)-PGJ(2) and similar prostaglandins.

引用

页码：372 / 374

页数：3

共 50 条

[21] Chiral, cross-conjugated isopolydiacetylenes
Lewis, Chad A.
Tykwinski, Rik R.
CHEMICAL COMMUNICATIONS, 2006, (34) : 3625 - 3627
[22] BASICITY OF CROSS-CONJUGATED KETOSTEROIDS
KOKOCINSKA, H
ZALEWSKI, RI
BULLETIN DE L ACADEMIE POLONAISE DES SCIENCES-SERIE DES SCIENCES CHIMIQUES, 1977, 25 (12): : 915 - 920
[23] Diruthenium-DMBA compounds bearing extended cross-conjugated ligandsd
Natoli, Sean N.
Zeller, Matthias
Ren, Tong
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 847 : 90 - 96
[24] The emergence of the cyclopentenone prostaglandins as important, biologically active compounds
Roberts, SM
Santoro, MG
Sickle, ES
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (15): : 1735 - 1742
[25] Synthesis of cross-conjugated dienic alcohols
Gamez, P
Ariente, C
Goré, J
Cazes, B
TETRAHEDRON, 1998, 54 (49) : 14825 - 14834
[26] Cross-conjugated polyenones in molecular chemistry
Marchand, N
Gree, R
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1996, 133 (11): : 1037 - 1051
[27] Design and synthesis of cross-conjugated macrocycles
Campbell, K
Pawlowska, M
Tykwinski, RR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U311 - U311
[28] Stable Cross-Conjugated Tetrathiophene Diradical
Zhang, Cheng
Medina Rivero, Samara
Liu, Wuyue
Casanova, David
Zhu, Xiaozhang
Casado, Juan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (33) : 11291 - 11295
[29] Synthesis and characterization of cross-conjugated polyenynes
Zhao, YM
McDonald, R
Tykwinski, RR
CHEMICAL COMMUNICATIONS, 2000, (01) : 77 - 78
[30] Anionic cyclization of a cross-conjugated enediyne
Eshdat, L
Berger, H
Hopf, H
Rabinovitz, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) : 3822 - 3823

← 1 2 3 4 5 →