Synthesis of [13C6]3,4-diaminobenzoic acid as a precursor for stable isotope labeled benzimidazoles

被引：2

作者：

Donahue, Matthew G. ^{[1
]}

Jentsch, Nicholas G. ^{[1
]}

Simons, Casey R. ^{[1
]}

机构：

[1] Univ Southern Mississippi, Dept Chem & Biochem, Hattiesburg, MS 39402 USA

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 17期

基金：

美国国家科学基金会;

关键词：

Benzimidazole; Carbon-13; Isotope; Medicinal chemistry; METABOLISM;

D O I：

10.1016/j.tetlet.2017.03.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of [C-13(6)]3,4-diaminobenzoic acid from commercially available [(13)C(6)laniline is described in six steps. Salient features of this route include the preparation of a differentially protected 3,4-diaminobenzonitrile, hydrogen gas free aromatic nitro group reduction with ammonium formate and facile benzimidazole ring closure of the ortho-arylenediamine with triethylorthoformate. This stable labeled 3,4-diaminobenzoic acid is an ideal [M+6]isotopomer to synthesize complex benzimidazole fragments for mass spectrometry internal assays. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：1692 / 1694

页数：3

共 24 条

[1] SYNTHESIS OF 1-(2-ETHOXYETHYL)-2-(4-METHYL-1-HOMOPIPERAZINYL)-[2-C-14]BENZIMIDAZOLEDIFUMARATE([C-14]KB-2413) [J].

AWATA, N ;

SATOMI, O .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1987, 24 (03) :331-338

[2] The therapeutic journey of benzimidazoles: A review [J].

Bansal, Yogita ;

Silakari, Om .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (21) :6208-6236

[3]

Brewster RQ, 1931, ORG SYNTH, V11, P62

[4]

Cuong LD, 1973, B SOC CHIM FR, V3317

[5] Hydrogenation on palladium-containing granulated catalysts - 3. Synthesis of aminobenzimidazoles by catalytic hydrogenation of dinitroanilines [J].

Elkin, V. V. ;

Tolkacheva, L. N. ;

Chernysheva, N. B. ;

Karmanova, I. B. ;

Konyushkin, L. D. ;

Semenov, V. V. .

RUSSIAN CHEMICAL BULLETIN, 2007, 56 (06) :1216-1226

[6] Benzimidazole: An emerging scaffold for analgesic and anti-inflammatory agents [J].

Gaba, Monika ;

Singh, Sarbjot ;

Mohan, Chander .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 76 :494-505

[7] THE METABOLISM OF BENZIMIDAZOLE ANTHELMINTICS [J].

GOTTSCHALL, DW ;

THEODORIDES, VJ ;

WANG, R .

PARASITOLOGY TODAY, 1990, 6 (04) :115-&

[8] Isotopic Labeling of Metabolites in Drug Discovery Applications [J].

Iglesias, Jacobo ;

Sleno, Lekha ;

Volmer, Dietrich A. .

CURRENT DRUG METABOLISM, 2012, 13 (09) :1213-1225

[9]

Kholkor PS, 1974, KHIM GETEROTSIKL, V11, P1547

[10]

Kurti L., 2005, APPL NAMED REACTIONS

← 1 2 3 →