Synthesis and biological evaluation of 10-benzyloxy-Narciclasine

被引：4

作者：

Ticli, Vincenzo ^{[1
]}

Zhao, Zhenze ^{[2
]}

Du, Liqin ^{[2
]}

Kornienko, Alexander ^{[2
]}

Hudlicky, Tomas ^{[1
]}

机构：

[1] Brock Univ, Dept Chem, 1812 Sir Isaac Brock Way, St Catharines, ON L2R 3A1, Canada

[2] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA

来源：

TETRAHEDRON | 2021年 / 101卷

基金：

加拿大自然科学与工程研究理事会; 美国国家卫生研究院; 加拿大创新基金会;

关键词：

Chemoenzymatic; Synthesis; Natural products; Narciclasine; Enantioselective synthesis; INTRAMOLECULAR HECK REACTION; AMARYLLIDACEAE CONSTITUENTS; ENANTIOSELECTIVE SYNTHESIS; NARCICLASINE ALKALOIDS; AROMATIC-HYDROCARBONS; OXIDATIVE-DEGRADATION; ANTINEOPLASTIC AGENTS; PANCRATISTATIN; (+)-PANCRATISTATIN; (+)-NARCICLASINE;

D O I：

10.1016/j.tet.2021.132505

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene dioxygenase-mediated hydroxylation, nitroso Diels-Alder reaction and intramolecular Heck cyclization. The unnatural derivative of narciclasine was subjected to biological evaluation and its activity was compared to other C-10 and C-7 compounds prepared previously. (c) 2021 Elsevier Ltd. All rights reserved.

引用

页数：10

共 50 条

[41] Synthesis and Biological Evaluation of Nonaprenylsulfates
Ravada, Suryachandra R.
Emani, Lakshmareddy
Manilla, Ganeswara R.
Golakoti, Trimurtulu
NATURAL PRODUCT COMMUNICATIONS, 2013, 8 (11) : 1595 - 1598
[42] Synthesis and Biological Evaluation of Quinaldopeptin
Katayama, Katsushi
Okamura, Takuya
Sunadome, Takuya
Nakagawa, Koji
Takeda, Hiroshi
Shiro, Motoo
Matsuda, Akira
Ichikawa, Satoshi
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (06): : 2580 - 2590
[43] Design, Synthesis, Biological Evaluation and Docking Studies of 2-hydroxy-4-benzyloxy Chalcone Derivatives as Multifunctional Agents for the Treatment of Alzheimer's Disease
Li, Wei
Huang, Jing
Chen, Zhixin
Zhang, Dan
He, Lin
Guo, Yan
Zhong, Lei
Yang, Chenwu
Yang, Chunyan
Zeng, Mei
Zhu, Jiang
Cao, Zhongcheng
CURRENT MEDICINAL CHEMISTRY, 2025,
[44] Synthesis and Biological Evaluation of Novel 10-Substituted-7-ethyl-10-hydroxycamptothecin (SN-38) Prodrugs
Zhou, Mo
Liu, Meixia
He, Xinhua
Yu, Hong
Wu, Di
Yao, Yishan
Fan, Shiyong
Zhang, Ping
Shi, Weiguo
Zhong, Bohua
MOLECULES, 2014, 19 (12) : 19718 - 19731
[45] Montmorillonite K10 Clay Catalyzed Synthesis of Novel β-Aminocarbonyl Compounds and Their Biological Evaluation
Rambabu, Gottimukkala
Kiran, Yarragudi Bathal Reddy
Tarakeswar, Yadamari
Khalivulla, Shaik Ibrahim
Barbosa, Luiz Claudio Almeida
Vijayakumar, Vijayaparthasarathi
CHEMISTRY & BIODIVERSITY, 2022, 19 (10)
[46] Synthesis and in vitro biological evaluation of pyrazole group-containing analogues for PDE10A
Li, Junfeng
Jin, Hongjun
Zhou, Haiying
Rothfuss, Justin
Tu, Zhude
MEDCHEMCOMM, 2013, 4 (02) : 443 - 449
[47] Synthesis and Biological Evaluation of 10-Substituted Camptothecin Derivatives with Improved Water Solubility and Activity
Yang, Xue-Yan
Zhao, Hong-Yi
Lei, Hao
Yuan, Bo
Mao, Shuai
Xin, Minghang
Zhang, San-Qi
CHEMMEDCHEM, 2021, 16 (06) : 1000 - 1010
[48] Design, synthesis of 10-alkoxy-5-spiro CPT and preliminary biological evaluation in vitro
Ke, Xi
Wang, Xianheng
Liu, Yuan
Wang, Yuhe
Zhao, Changkuo
TETRAHEDRON, 2023, 135
[49] Synthesis and biological evaluation of 10-photoaffinity, 7-radiolabeled paclitaxel analogs.
Flaherty, PT
Liu, YB
Georg, GI
Himes, RH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U16 - U16
[50] Synthesis and biological evaluation of steroidal derivatives as selective inhibitors of AKR1B10
Zhang, Wei
Wang, Ling
Zhang, Liping
Chen, Wenli
Chen, Xinying
Xie, Minyu
Yan, Guangmei
Hu, Xiaopeng
Xu, Jun
Zhang, Jingxia
STEROIDS, 2014, 86 : 39 - 44

← 1 2 3 4 5 →