Facile Synthesis of Thalidomide

被引：11

作者：

Binh Duong Vu ^{[1
]}

Ngoc Minh Ho Ba ^{[1
]}

Dinh Chau Phan ^{[2
]}

机构：

[1] Vietnam Mil Med Univ, R&D Drug Ctr, Phuc La Ward, 160 Phung Hung Str, Hanoi 10000, Vietnam

[2] Hanoi Univ Sci & Technol, Sch Chem Engn, Bach Khoa Ward, 1 Dai Co Viet Str, Hanoi 10000, Vietnam

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2019年 / 23卷 / 07期

关键词：

thalidomide; N-phthaloyl-DL-glutamic anhydride; leprosy; rheumatoid arthritis; neoplastic diseases; multiple myeloma; EFFICIENT; ANALOGS;

D O I：

10.1021/acs.oprd.9b00122

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report a simple and facile procedure for the preparation of thalidomide in two steps with a high overall yield (56%). The preparation was composed of a reaction between anhydride phthalic and L-glutamic acid to form N-phthaloyl-DL-glutamic acid (IV), and a cyclization step using IV reacted with ammonium acetate in diphenyl ether to create thalidomide. Reaction parameters reaction time, temperature, solvent, and molar ratio of reagents in the procedure are optimized so that the reaction performance is highest while ensuring environmental friendliness. Moreover, this process has great potential for the industrial scale of thalidomide. These compounds were identified through IR, MS, H-1 NMR, and C-13 NMR.

引用

页码：1374 / 1377

页数：4

共 50 条

[1] A synthesis of thalidomide
Chang, MY
Chang, CH
Chen, ST
Chang, NC
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (03) : 383 - 385
[2] Microwave Assisted Synthesis of Thalidomide on Hectogram Scale
Trong Diep Nguyen
Ngoc Minh Ho Ba
Dinh Chau Phan
Binh Duong Vu
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2022, 54 (03) : 294 - 298
[3] A synthesis of racemic thalidomide
Chang, MY
Chen, ST
Chang, NC
SYNTHETIC COMMUNICATIONS, 2003, 33 (08) : 1375 - 1382
[4] Synthesis and Evaluation of Thalidomide and Phthalimide Esters as Antitumor Agents
Zahran, Magdy A. H.
Abdin, Yasmin G.
Osman, Amany M. A.
Gamal-Eldeen, Amira M.
Talaat, Roba M.
Pedersen, Erik B.
ARCHIV DER PHARMAZIE, 2014, 347 (09) : 642 - 649
[5] Thalidomide inhibited the synthesis of IgM and IgG whereas Thalidomide plus Dexamethasone and Dexamethasone alone acted as co-stimulants with pokeweed and enhanced their synthesis
Shannon, E. J.
Sandoval, F.
INTERNATIONAL IMMUNOPHARMACOLOGY, 2010, 10 (04) : 487 - 492
[6] Thalidomide derivatives as nanomolar human neutrophil elastase inhibitors: Rational design, synthesis, antiproliferative activity and mechanism of action
Donarska, Beata
Slawinska-Brych, Adrianna
Mizerska-Kowalska, Magdalena
Zdzisinska, Barbara
Plazinski, Wojciech
Laczkowski, Krzysztof Z.
BIOORGANIC CHEMISTRY, 2023, 138
[7] A Novel Green Synthesis of Thalidomide and Analogs
Benjamin, Ellis
Hijji, Yousef M.
JOURNAL OF CHEMISTRY, 2017, 2017
[8] Recent studies on the thalidomide and its derivatives
Laczkowski, Krzysztof Z.
Baranowska-Laczkowska, Angelika
FUTURE MEDICINAL CHEMISTRY, 2018, 10 (18) : 2133 - 2136
[9] Synthesis of 1,2,3-triazole 'click' analogues of thalidomide
Ronnebaum, Jarrid M.
Luzzio, Frederick A.
TETRAHEDRON, 2016, 72 (40) : 6136 - 6141
[10] Lenalidomide and thalidomide in the treatment of chronic pain
Asher, Christopher
Furnish, Timothy
EXPERT OPINION ON DRUG SAFETY, 2013, 12 (03) : 367 - 374

← 1 2 3 4 5 →