Total synthesis of (±) commiphoranes C-D and their epimers

被引：0

作者：

Liu, Xiaoyu ^{[1
]}

Deng, Haidong ^{[2
]}

Jiang, Yingjun ^{[1
]}

Cao, Yang ^{[1
]}

Wang, Zhe ^{[1
]}

Jiao, Xiaozhen ^{[1
]}

Xie, Ping ^{[1
]}

机构：

[1] Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing Key Lab Act Subst Discovery & Druggabil E, Beijing 100050, Peoples R China

[2] Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, Dept Pharmacol, Beijing Key Lab New Drug Mech & Pharmacol Evaluat, Beijing 100050, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 10期

基金：

中国国家自然科学基金;

关键词：

ACID; ESTERS; ARYL;

D O I：

10.1039/d2ob00158f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-) Commiphorane C, (+/-) commiphorane D, and their two isomers were synthesized through a linear synthesis strategy in 14 steps. Key features of the strategy include the construction of the relative configurations of C-5 and C-6 via aldehyde crotylation followed by the Mitsunobu reaction and ring A via an intramolecular Aldol reaction. The biological evaluation revealed that (+/-) commiphorane C and (+/-) isomer-1 significantly attenuated the overproduction of fibronectin, collagen I, and alpha-SMA in TGF-beta 1-induced rat renal proximal tubular cells. Intermediate (+/-) 11 significantly decrease the overexpression of collagen I. Cytotoxicity studies showed that 1a-1d and (+/-) 11 were not toxic to NRK-52E cells.

引用

页码：2102 / 2108

页数：7

共 15 条

[1] Myrrh and trematodoses in Egypt: An overview of safety, efficacy and effectiveness profiles
Abdul-Ghani, Rashad A.
Loutfy, Naguiba
Hassan, Azza
[J]. PARASITOLOGY INTERNATIONAL, 2009, 58 (03) : 210 - 214
[2] Gastric antiulcer and cytoprotective effect of Commiphora molmol in rats
AlHarbi, MM
Qureshi, S
Raza, M
Ahmed, MM
Afzal, M
Shah, AH
[J]. JOURNAL OF ETHNOPHARMACOLOGY, 1997, 55 (02) : 141 - 150
[3] TGF-β signaling in fibrosis
Biernacka, Anna
Dobaczewski, Marcin
Frangogiannis, Nikolaos G.
[J]. GROWTH FACTORS, 2011, 29 (05) : 196 - 202
[4] Regiodivergent Halogenation of Vinylogous Esters: One-Pot, Transition-Metal-Free Access to Differentiated Haloresorcinols
Chen, Xiaohong
Martinez, Jenny S.
Mohr, Justin T.
[J]. ORGANIC LETTERS, 2015, 17 (02) : 378 - 381
[5] Commiphoranes A-D, Carbon Skeletal Terpenoids from Resina Commiphora
Dong, Lu
Cheng, Li-Zhi
Yan, Yong-Ming
Wang, Shu-Mei
Cheng, Yong-Xian
[J]. ORGANIC LETTERS, 2017, 19 (01) : 286 - 289
[6] PALLADIUM-CATALYZED VINYLIC HYDROGEN SUBSTITUTION REACTIONS WITH ARYL, BENZYL, AND STYRYL HALIDES
HECK, RF
NOLLEY, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) : 2320 - &
[7] The effect of acid strength on the Mitsunobu esterification reaction: Carboxyl vs hydroxyl reactivity
Hughes, DL
Reamer, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 2967 - 2971
[8] Acceleration effect of Lewis acid in allylboration of aldehydes: Catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols
Ishiyama, T
Ahiko, T
Miyaura, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (42) : 12414 - 12415
[9] Total syntheses of O4,O9-dimethylstealthins A and C
Koyama, H
Kamikawa, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02): : 203 - 209
[10] Latha Subbiah, 2021, Cardiovascular & Hematological Agents in Medicinal Chemistry, V19, P101, DOI 10.2174/1871525718666200702125558

← 1 2 →