(Z)-2-[2-(三苯甲基氨基)噻唑-4-基]-2-(三苯甲基氧基亚氨基)乙酸乙酯 | 69689-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: (Z)-2-[2-(三苯甲基氨基)噻唑-4-基]-2-(三苯甲基氧基亚氨基)乙酸乙酯
• 英文名称: ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate
• 英文别名: (2-tritylamino-thiazol-4-yl)-(Z)-trityloxyimino-acetic acid ethyl ester；(Z)-ethyl-2-(2-(tritylamino)thiazol-4-yl)-2-(trityloxyimino) acetate；(Z)-ethyl 2-(2-(tritylamino)thiazol-4-yl)-2-(trityloxyimino)acetate；(Z)-(2-tritylamino-thiazol-4yl)-2-trityloxyimino ethyl acetate；(Z)-2-[2-(Tritylamino)thiazol-4-yl]-2-(trityloxyimino)acetic Acid Ethyl Ester；ethyl (2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetate
• CAS: 69689-86-7
• 化学式: C₄₅H₃₇N₃O₃S
• 分子量: 699.873
• InChiKey: FKRLRAWKHDWOEM-BCUHICPISA-N

物化性质

• 沸点：
  813.2±75.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-2-[2-(三苯甲基氨基)噻唑-4-基]-2-(三苯甲基氧基亚氨基)乙酸乙酯 在 sodium hydroxide 、 甲酸 、 苯甲醚 、 N,N-二甲基苯胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 头孢地尼
  参考文献：
  名称：

  An alternative procedure for preparation of cefdinir

  摘要：

  Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7beta-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7beta-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3-vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.

  DOI：

  10.1016/s0014-827x(03)00063-6
• 作为产物：
  描述：

  ethyl 2-(hydroxyimino)-3-oxybutyrate 在 磺酰氯 、 TEA 、 溶剂黄146 作用下， 以 氯仿 、 N,N-二甲基乙酰胺 为溶剂， 反应 5.5h， 生成 (Z)-2-[2-(三苯甲基氨基)噻唑-4-基]-2-(三苯甲基氧基亚氨基)乙酸乙酯
  参考文献：
  名称：

  An alternative procedure for preparation of cefdinir

  摘要：

  Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7beta-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7beta-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3-vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.

  DOI：

  10.1016/s0014-827x(03)00063-6

文献信息

• [EN] CARBACEPHEM BETA-LACTAM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES DE TYPE BÉTA-LACTAME À BASE DE CARBACÉPHÈME
  申请人：ACHAOGEN INC

  公开号：WO2010030810A1

  公开（公告）日：2010-03-18

  Carbacephem β-lactam antibiotics having structure (I) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, X, R1 and R2 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

  揭示了具有结构（I）的碳青霉烯β-内酰胺类抗生素，包括立体异构体、药用盐、酯及其前药，其中Ar2、X、R1和R2如本文所定义。这些化合物对于治疗细菌感染特别有效，尤其是由耐甲氧西林金黄色葡萄球菌引起的感染。
• [EN] CARBACEPHEM BETA-LACTAM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES BÊTA-LACTAMES CARBACÉPHÈMES
  申请人：ACHAOGEN INC

  公开号：WO2010123997A1

  公开（公告）日：2010-10-28

  Carbacephem β-lactam antibiotics having chemical structures (I) and (II) are disclosed: including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, R1, R2 and R6 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

  Carbacephem β-内酰胺类抗生素具有化学结构（I）和（II）如下：包括立体异构体、药用可接受的盐、酯和前药，其中Ar2、R1、R2和R6如本文所定义。这些化合物对治疗细菌感染特别有效，尤其是由耐甲氧西林金黄色葡萄球菌引起的感染。
• Synthesis of HR 916 K: An Efficient Route to the Pure Diastereomers of the 1-(Pivaloyloxy)ethyl Esters of Cephalosporins
  作者：Elisabeth Defoßa、Gerd Fischer、Uwe Gerlach、Rolf Hörlein、Dieter Isert、Norbert Krass、Rudolf Lattrell、Ulrich Stache、Theo Wollmann

  DOI：10.1002/jlac.199619961107

  日期：1996.11

  HR 916 K (5), the 1-(S)-(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, exhibits a significantly higher oral bioavailability than the 1-(R) diastereomer HR 916 J. An efficient synthesis of HR 916 K was developed. The separation of the diastereomers was achieved by precipitation of the 1-(R)-hydrochloride 9 followed by crystallization of the 1-(S)-amine 10 (de > 96%). The 1-(R) diastereomer

  HR 916 K（5）是头孢菌素头孢达肟的1-（S）-（新戊酰氧基）乙基前药酯，其口服生物利用度明显高于1-（R）非对映异构体HR 916J。HR 916 K的有效合成发展了。非对映异构体的分离通过沉淀1-（R）-盐酸盐9，然后结晶1-（S）-胺10（de＞ 96％）来实现。通过酸性皂化或酶促裂解将1-（R）非对映异构体9再循环至AMCA（7）。胺10用巯基苯并噻唑硫酯或由羧酸13和14制备的混合酸酐将其酰化，几乎可以定量收率。肟的脱保护和甲苯磺酸酯的形成是一步进行的。使用硫酯18，我们以42％的收率从AMCA（7）获得了HR 916 K（5）。
• Stable bioavailable crystalline form or cefdinir and a process for the preparation thereof
  申请人：Singh Pal Girij

  公开号：US20050245738A1

  公开（公告）日：2005-11-03

  The present invention relates to a stable and bioavailable crystalline form of a third generation cephalosporin antibiotic, cefdinir and a process for the preparation thereof. The present invention also relates to a pharmaceutical composition containing the novel crystalline cefdinir, useful in the treatment of maladies such as bacterial infections.

  本发明涉及第三代头孢菌素抗生素头孢噻肟的稳定且生物利用度高的结晶形式，以及其制备方法。本发明还涉及一种含有新型结晶头孢噻肟的药物组合物，可用于治疗细菌感染等疾病。
• Cephalosporines a chaines amino-2 thiazolyl-4 acetyles
  作者：R. Bucourt、R. Heymes、A. Lutz、L. Pénasse、J. Perronnet

  DOI：10.1016/0040-4020(78)89034-6

  日期：1978.1

  The syntheses of 2-(2-amino-4-thiazolyl) 2-(hydroxy or alkoxy)-imino acetic acid derivatives, with the anti (E) and syn (Z) configurations, are described. By means of these compounds, the acylation of the amino-group of 7β-amino cephalosporanic acid (7-ACA) has been achieved. The two resulting series of cephalosporin derivatives-anti and syn-are markedly different with respect to their antibiotic activity

  描述了具有反（E）和顺（Z）构型的2-（2-氨基-4-噻唑基）2-（羟基或烷氧基）-亚氨基乙酸衍生物的合成。通过这些化合物，已经实现了7β-氨基头孢烷酸（7-ACA）的氨基的酰化。这两个由此带来的一系列的头孢derivatives-防和顺式相对于它们的抗菌活性-are明显不同。一些合成化合物具有迄今为止所观察到的最高的抗菌活性。