2-(2-triphenylmethylaminothiazol-4-yl)-2-hydroxyiminoacetic acid allyl ester | 94796-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(2-triphenylmethylaminothiazol-4-yl)-2-hydroxyiminoacetic acid allyl ester
• 英文别名: allyl 2-[2-(triphenylmethyl)aminothiazol-4-yl]-2-hydroxyiminoacetate；allyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-(hydroxyimino)acetate；allyl [2-(tritylamino)thiazol-4-yl)-2-hydroxyiminoacetate；allyl(Z)-2-(2-trityl-aminothiazole-4-yl)2-hydroxyiminoacetate；allyl (Z)-2-hydroxyimino-2-(2-tritylaminothiazol-4-yl)acetate；prop-2-enyl (2Z)-2-hydroxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate
• CAS: 94796-25-5
• 化学式: C₂₇H₂₃N₃O₃S
• 分子量: 469.564
• InChiKey: KCASOAUQVCSNPJ-KRUMMXJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-triphenylmethylaminothiazol-4-yl)-2-hydroxyiminoacetic acid allyl ester 在 potassium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 allyl 2-(tritylaminothiazol-4-yl)-2-[(R)-(+)-1-(diphenylmethoxycarbonyl)prop-1-oxyimino] acetate
  参考文献：
  名称：

  Cephalosporin compounds

  摘要：

  本发明涉及新的头孢菌素化合物、药学上可接受的无毒盐、生理上水解的酯、水合物、溶剂合物及其同分异构体，具有强大而广泛的抗菌活性。本发明的化合物在头孢菌素核的3位具有(4-氨基-1-取代-烷基嘧啶-4-基)硫甲基基团，具体表示如下式(I)：其中：R^1是氢原子或C.sub.1-4烷基、C.sub.2-4烯基、C.sub.2-4炔基或--C(R^A)(R^B)COOH基团，其中R^A和R^B独立地是氢原子或C.sub.1-4烷基，或者与它们连接的碳原子一起形成C.sub.3-7环烷基基团；R^2是未取代或取代的氨基、C.sub.1-4烷基或C.sub.3-7环烷基基团；n是一个范围从2到7的整数。

  公开号：

  US05416081A1
• 作为产物：
  描述：

  烯丙醇 、 ethyl (Z)-2-hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)acetate 在 sodium ethanolate 作用下， 反应 4.0h， 以70%的产率得到2-(2-triphenylmethylaminothiazol-4-yl)-2-hydroxyiminoacetic acid allyl ester
  参考文献：
  名称：

  Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

  摘要：

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00261-8

文献信息

• Antibacterial agent for mammal use comprising cephalosporin derivatives
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：US04810702A1

  公开（公告）日：1989-03-07

  Cephalosporin compounds having 2-(2-aminothiazol-4-yl)-2(1S)-carboxyethoxyimino}acetyl group on the side chain at the 7-position thereof and 1-ethylpyridinium-4-ylthiomethyl group on the side chain at the 3-position thereof or non-toxic salts thereof are excellent antibacterial agents for mammals including human. The cephalosporin derivatives have low toxicity.

  头孢菌素化合物，其在7位侧链上具有2-(2-氨基噻唑-4-基)-2(1S)-羧乙氧基亚氨基}乙酰基团，在3位侧链上具有1-乙基吡啶鎓-4-基硫甲基团，或其非毒性盐，是对包括人类在内的哺乳动物的优秀抗菌剂。这些头孢菌素衍生物具有低毒性。
• Novel cephalosporin compounds
  申请人：LUCKY LTD.

  公开号：EP0604920A1

  公开（公告）日：1994-07-06

  The present invention relates to novel cephalosporin compounds, pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates and isomers thereof which possess potent and broad antibacterial activities. The compounds of the present invention have a (4-amino-1-substituted-alkapyrimidinium-4-yl)thiomethyl group in 3-position of the cephem nucleus and is specifically represented by the following formula(I): wherein: R¹ isa hydrogen atom or, a C₁₋₄ alkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl or -C(RA)(RB)COOH group wherein RA and RB are independently a hydrogen atom or a C₁₋₄ alkyl group, or form a C₃₋₇ cycloalkyl group together with the carbon atom to which they are attached; R² isan unsubstituted or substituted amino, C₁₋₄ alkyl or C₃₋₇ cycloalkyl group; and n isan integer ranging from 2 to 7.

  本发明涉及新型头孢菌素化合物，其具有强大和广泛的抗菌活性的药用可接受的无毒盐、生理水解酯、水合物、溶剂合物和其异构体。本发明的化合物在头孢菌素核的3-位置具有(4-氨基-1-取代-烷基嘧啶-4-基)硫甲基基团，具体由以下式(I)表示：其中：R¹是氢原子或C₁₋₄烷基、C₂₋₄烯基、C₂₋₄炔基或-C(RA)(RB)COOH基团，其中RA和RB独立地是氢原子或C₁₋₄烷基，或者与它们所连接的碳原子一起形成C₃₋₇环烷基基团；R²是未取代或取代的氨基、C₁₋₄烷基或C₃₋₇环烷基基团；n是一个范围从2到7的整数。
• Novel cephalosporin compounds and processes for the preparation thereof
  申请人：LUCKY LTD.

  公开号：EP0584797A3

  公开（公告）日：1994-06-08

  The present invention relates to novel cephalosporin compounds, pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates and isomers thereof which possess potent and broad antibacterial activities. The compounds of the present invention have a (1,5,6-substituted-4-aminopyrimidinium-2-yl)thiomethyl group in 3-position of the cephem nucleus and is specifically represented by the following formula(I):

  本发明涉及新型头孢菌素化合物，药学上可接受的无毒盐、生理可水解的酯、水合物和溶剂合物及其异构体，具有强大和广泛的抗菌活性。本发明的化合物在头孢菌素核的3位具有(1,5,6-取代-4-氨基嘧啶-2-基)硫甲基基团，具体由以下式(I)表示：
• Cephalosporin compounds and their use
  申请人：Ishimaru, Toshiyasu

  公开号：EP0400805A1

  公开（公告）日：1990-12-05

  A cephalosporin compound of the formula (I): wherein X and Y may be the same or different and are a hydrogen or halogen atom; Z is a hydrogen or halogen atom, -CH=CH₂, -CH=CH-CH₃, -OR¹, -SR² or -CH₂W in which R¹ and R² are a lower alkyl group and W is a hydrogen atom or a nucleophilic residue, its pharmaceutically acceptable salt, a process for preparing the same and their antibacterial composition.

  一种头孢菌素化合物，其化学式为（I）：其中X和Y可能相同或不同，为氢原子或卤素原子；Z为氢原子或卤素原子，-CH=CH₂，-CH=CH-CH₃，-OR¹，-SR²或-CH₂W，其中R¹和R²为较低的烷基基团，W为氢原子或亲核残基，以及其药用可接受盐、制备方法及其抗菌组合物。
• Cephalosporin compounds and processes for the preparation thereof
  申请人：LUCKY LTD.

  公开号：EP0582261A1

  公开（公告）日：1994-02-09

  The present invention relates to a cephalosporin compound including the pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates thereof of the formula(I) and its isomers: wherein: R¹ isa C₁₋₄ alkyl, C₃₋₄ alkenyl, C₃₋₄ alkynyl or -C(Ra)(Rb)-COOH wherein Ra and Rb are, independently of each other, a hydrogen or a C₁₋₄ alkyl group, respectively, or jointly form a C₃₋₇ cycloalkyl group together with the carbon atoms to which they are attached; R² isa hydrogen or an amino which may be substituted or unsubstituted, alkoxy or heterocyclic group which is linked with a nitrogen atom; R³ isa hydrogen or a C₁₋₄ alkyl, amino, aminomethyl, hydroxy, hydroxymethyl, carboxy or carboxymethyl group; R⁴ isa hydrogen or a C₁₋₄ alkyl, amino, hydroxy, hydroxyalkl, acetamide, carboxyalkyl or sulfonylethyl group; R⁵ isa hydrogen or a C₁₋₄ alkyl, amino, carboxy, carboxyalkyl or hydroxy group; and Q and T areindependently CH or N, provided that R² is an amino group when T is N.

  本发明涉及一种头孢菌素化合物，包括其药学上可接受的非毒性盐、生理水解酯、水合物和溶剂化合物，其分子式为(I)及其异构体：其中：R¹为C₁₋₄烷基、C₃₋₄烯基、C₃₋₄炔基或-C(Ra)(Rb)-COOH，其中Ra和Rb分别为氢或C₁₋₄烷基，或者共同形成与它们连接的碳原子一起的C₃₋₇环烷基；R²为氢或与氮原子连接的可取代或不可取代的氨基、烷氧基或杂环基团；R³为氢或C₁₋₄烷基、氨基、氨甲基、羟基、羟甲基、羧基或羧甲基基团；R⁴为氢或C₁₋₄烷基、氨基、羟基、羟基烷基、乙酰胺基、羧基烷基或磺酰乙基基团；R⁵为氢或C₁₋₄烷基、氨基、羧基、羧基烷基或羟基基团；Q和T独立地为CH或N，条件是当T为N时，R²为氨基团。