(Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>ethanamide | 89876-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>ethanamide
• 英文别名: S-(2-benzothiazolyl) (2-amino-4-thiazolyl)-(Z)-<(2-amino-2-oxoethoxy)imino>thioacetate；S-(1,3-benzothiazol-2-yl) (2Z)-2-(2-amino-2-oxoethoxy)imino-2-(2-amino-1,3-thiazol-4-yl)ethanethioate
• CAS: 89876-15-3
• 化学式: C₁₄H₁₁N₅O₃S₃
• 分子量: 393.471
• InChiKey: DHFUXTRUZCOOBS-ODLFYWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  215
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>ethanamide 、 (6R-trans)-7-amino-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid trifluoroacetic acid salt 在 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 <6R-<6α,7β(Z)>>-7-<<<(2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates

  摘要：

  A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities.

  DOI：

  10.1021/jm00113a026

文献信息

• A facile and general synthesis of 3-(acyloxy)cephalosporins
  作者：C. C. Wei、D. Bartkovitz、K. F. West

  DOI：10.1021/jo00040a057

  日期：1992.7
• ISOOXACEPHEM DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0879237A1

  公开（公告）日：1998-11-25
• US5811419A
  申请人：——

  公开号：US5811419A

  公开（公告）日：1998-09-22
• [EN] ISOOXACEPHEM DERIVATIVES<br/>[FR] DERIVES D'ISOOXACEPHEME
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：WO1997026260A1

  公开（公告）日：1997-07-24

  (EN) The present invention relates to isooxacephem derivatives of general formula (I), wherein R1 is hydrogen or an acyl group derived from a carboxylic acid; R2 is hydrogen, hydroxy, lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aryl-lower alkyl, aryl, aryloxy, aryl-lower alkoxy or a heterocyclic ring; the lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aryl-lower alkyl, aryl, aryloxy, aryl-lower alkoxy and the heterocyclic ring being unsubstituted or substituted with at least one group selected from carboxy, amino, nitro, cyano, lower alkyl, lower alkoxy, hydroxy, halogen, -CONR21R22, -N(R22)COOR23, R22CO-, R22OCO- or R22COO-, wherein R21 is hydrogen, lower alkyl, or cycloalkyl; R22 is hydrogen or lower alkyl; R23 is lower alkyl, lower alkenyl or a carboxylic acid protecting group; as well as readily hydrolyzable esters thereof, pharmaceutically acceptable salts of said compounds and hydrates of the compounds of formula (I) and of their esters and salts.(FR) La présente invention se rapporte à des dérivés d'isooxacéphène de la formule générale (I), dans laquelle R1 représente hydrogène ou un groupe acyle dérivé d'un acide carboxylique, R2 représente hydrogène, hydroxy, alkyle inférieur, cycloalkyle, alcoxy inférieur, alcényle inférieur, cycloalcényle, alcynyle inférieur, aryl-alkyle inférieur, aryle, aryloxy, aryl-alcoxy inférieur ou un noyau hétérocyclique; alkyle inférieur, cycloalkyle, alcoxy inférieur, alcényle inférieur, cycloalcényle, alcynyle inférieur, aryl-alkyle inférieur, aryle, aryloxy, aryl-alcoxy inférieur et le noyau hétérocyclique n'étant pas substitués ou l'étant par au moins un groupe choisi parmi carboxy, amino, nitro, cyano, alkyle inférieur, alcoxy inférieur, hydroxy, halogène, -CONR21R22, -N(R22)COOR23, R22CO-, R22OCO- ou R22COO-, où R21 représente hydrogène, alkyle inférieur ou cycloalkyle, R22 représente hydrogène ou alkyle inférieur, R23 représente alkyle inférieur, alcényle inférieur ou un groupe protecteur d'acide carboxylique. L'invention concerne également des esters de ces composés, aisément hydrolysables, des sels, acceptables sur le plan pharmacologique, de ces composés ainsi que des hydrates de ces composés de la formule (I) de même que des esters et sels de ceux-ci.
• Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates
  作者：Harry A. Albrecht、George Beskid、Nafsika H. Georgopapadakou、Dennis D. Keith、Frederick M. Konzelmann、David L. Pruess、Pamela L. Rossman、Chung Chen Wei、James G. Christenson

  DOI：10.1021/jm00113a026

  日期：1991.9

  A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities.