用于抗体导向酶解前药疗法（ADEPT）的头孢烯衍生物的合成及1H和13C核磁共振全归属

Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches.

作者信息

Blau Lorena, Menegon Renato Farina, Ferreira Elizabeth Igne, Ferreira Antonio Gilberto, Boffo Elisangela Fabiana, Tavares Leila Aley, Heleno Vladimir Constantino Gomes, Chung Man-Chin

机构信息

Departamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, CP 502 - 14801-902, Araraquara, SP, Brazil.

出版信息

Molecules. 2008 Apr 10;13(4):841-54. doi: 10.3390/molecules13040841.

DOI:10.3390/molecules13040841

PMID:18463586

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6245275/

Abstract

We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4''-nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]- 5-dioxide (7) are also described, together with their total (1)H- and (13)C-NMR assignments.

摘要

我们报道了一种新型头孢菌素衍生物5-硫杂-1-氮杂双环-[4.2.0]辛-2-烯-2-羧酸-3-[[[(4''-硝基苯氧基)羰基]氧基]-甲基]-8-氧代-7-[(2-噻吩基氧乙酰基)氨基]-二苯甲酯-5-二氧化物（5）的合成及全核磁共振表征。该化合物可用作多种含氨基药物的载体。还描述了中间体产物5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸-3-[甲基4-(6-甲氧基喹啉-8-基氨基)戊基氨基甲酸酯]-8-氧代-7-[(2-噻吩基氧乙酰基)氨基]-二苯甲酯-5-二氧化物（6）的制备，以及抗疟原药伯氨喹前药5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸-3-[甲基4-(6-甲氧基喹啉-8-基氨基)戊基氨基甲酸酯]-8-氧代-7-[(2-噻吩基氧乙酰基)氨基]-5-二氧化物（7）的合成，以及它们的全氢谱和碳谱核磁共振归属。