Solid-phase synthesis of 6-sulfonylamino morphinan libraries

被引：0

作者：

Ohno, H

Kawamura, K

Otake, A

Nagase, H

Tanaka, H

Takahashi, T

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

[2] Toray Industries Ltd, Pharmaceut Res Lab, Dept Med Chem, Kamakura, Kanagawa 2488555, Japan

来源：

SYNLETT | 2002年 / 01期

关键词：

opioid; morphinan; solid-phase synthesis; ketones; sulfonamides;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A solid-phase synthesis of 6-sulfonylamino morphinan has been developed. The morphinan derivatives were designed as selective opioid ligands. The sulfonamide moiety was introduced by reductive amination of a ketone on solid phase, followed by sulfonylation of the resulting amine. Using this methodology, the synthesis of three combinatorial libraries was accomplished to prepare 339 morphinan derivatives with over 70% purity.

引用

页码：93 / 96

页数：4

共 50 条

[1] Solid-phase synthesis of triazinobenzimidazole libraries
Nefzi, Adel
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3443 - U3444
[2] Solid-phase synthesis: Applications to combinatorial libraries
Choong, IC
Ellman, JA
ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 31, 1996, 31 : 309 - 318
[3] Traceless solid-phase synthesis of benzimidazole libraries
Huang, WL
Scarborough, RM
PEPTIDES FOR THE NEW MILLENNIUM, 2000, : 181 - 182
[4] Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries
Seeberger, PH
Haase, WC
CHEMICAL REVIEWS, 2000, 100 (12) : 4349 - +
[5] Parallel solid-phase synthesis of nucleoside phosphoramidate libraries
Jin, Y
Chen, XL
Côté, ME
Roland, A
Korba, B
Mounir, S
Iyer, RP
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (16) : 2057 - 2060
[6] An approach to carbohydrate solid-phase synthesis and carbohydrate libraries.
Joshi, S
Rodebaugh, R
Merritt, JR
Geysen, HM
FraserReid, B
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 17 - CARB
[7] Simultaneous solid-phase synthesis of quinoxalinone and benzimidazole scaffold libraries
Kou, Bin-Bin
Zhang, Fa
Yang, Tian-Ming
Liu, Gang
JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (06): : 841 - 847
[8] Solid-phase synthesis in the development of small-molecule libraries
Lloyd, AW
DRUG DISCOVERY TODAY, 1996, 1 (01) : 42 - 43
[9] Solid-phase synthesis of 2,4-diaminoquinazoline libraries
Dener, JM
Lease, TG
Novack, AR
Plunkett, MJ
Hocker, MD
Fantauzzi, PP
JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (06): : 590 - 597
[10] Synthesis of nucleoside libraries by solid-phase combinatorial strategies.
An, HY
Rong, F
Habib, Q
Amador, RB
Ding, Y
Gunic, E
Koh, YH
Chen, HM
Girardet, JL
Li, D
Huang, JF
Han, XG
Hong, Z
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U183 - U183

← 1 2 3 4 5 →