R-2-<(4-ethyl-2,3-dioxo-1-piperadinyl)formamido> phenylacetyl chloride | 64205-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: R-2-<(4-ethyl-2,3-dioxo-1-piperadinyl)formamido> phenylacetyl chloride
• 英文别名: (R)-α-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl chloride；(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl chloride
• CAS: 64205-06-7
• 化学式: C₁₅H₁₆ClN₃O₄
• 分子量: 337.763
• InChiKey: OXGIEQIKQQIROK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  R-2-<(4-ethyl-2,3-dioxo-1-piperadinyl)formamido> phenylacetyl chloride 在 silver(I) acetate 吡啶 、 硫化氢 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Allyl 6β-<(2R)-2-(4-Ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-6α-mercaptopenicillanate
  参考文献：
  名称：

  Milner, Peter H.; Stachulski, Andrew V., Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2343 - 2352

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙基双氧哌嗪酰氨苯乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 R-2-<(4-ethyl-2,3-dioxo-1-piperadinyl)formamido> phenylacetyl chloride
  参考文献：
  名称：

  3-（N-取代的吡啶鎓-4-硫代甲基）-7α-甲酰胺基头孢菌素的合成及生物活性。

  摘要：

  描述了一系列的3-（1-取代的吡啶鎓-4-硫代甲基）-7α-甲酰胺基头孢菌素的合成和抗菌活性。所有衍生物对细菌β-内酰胺酶均显示出良好的效力和稳定性。通过在C-7处引入侧链侧链并通过制备N-（取代的氨基）吡啶鎓衍生物，增强了用N-烷基吡啶鎓取代基所见的抗菌功效。

  DOI：

  10.7164/antibiotics.46.1279

文献信息

• 3-Trifluoromethylcephalosporins. II. Synthesis and in vitro antibacterial activities of 3-trifluoromethylcephalosporin derivatives.
  作者：YOICHI KAWANO、TAIICHIRO WATANABE、JUNICHI SAKAI、HIDETOSHI WATANABE、MITSUO NAGANO、TAKUZO NISHIMURA、TETSUO MIYADERA

  DOI：10.1248/cpb.28.70

  日期：——

  Various acylamido derivatives of 3-trifluoromethyl-3-cephem-4-carboxylic acid were synthesized and tested for in vitro antibacterial activities. The 3-trifluoromethylcephalosporin derivatives synthesized herein are 7α- and 7β-acylamido-3-cephem-, 7α- methoxy-7β-acylamido-3-cephem- and 7β-acylamido-2-cephem-4-carboxylic acids. Among these compounds, the R-mandelamido derivative (IIIb) showed the highest antibacterial activity against gram-negative bacteria at pH 7.0. The minimum inhibitory concentration values of the 2-thienylacetamido- and phenylglycylamido derivatives are compared with those of the 3-methyl- and 3-chloro analogs, and structure-activity relationships are discussed.

  合成了 3-三氟甲基-3-头孢-4-羧酸的各种酰氨基衍生物，并进行了体外抗菌活性测试。本文合成的 3-三氟甲基头孢菌素衍生物是 7α- 和 7β- 乙酰氨基-3-头孢-、7α-甲氧基-7β-乙酰氨基-3-头孢-和 7β- 乙酰氨基-2-头孢-4-羧酸。在这些化合物中，R-扁桃酰氨基衍生物（IIIb）在 pH 值为 7.0 时对革兰氏阴性菌的抗菌活性最高。将 2-噻吩乙酰胺基和苯基甘氨酰氨基衍生物的最小抑菌浓度值与 3-甲基和 3-氯类似物的最小抑菌浓度值进行了比较，并讨论了结构-活性关系。
• 2-Beta-substituted methyl-penam derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0287734A1

  公开（公告）日：1988-10-26

  Antibacterial agents have the formula (I) or are pharmaceutically acceptable salts or in vivo hydrolysable esters thereof: wherein R³ is phenyl, substituted phenyl, cyclohexenyl, cyclohexadienyl or an optionally substituted 5- or 6-­membered heterocyclic ring containing up to three hetero atoms selected from oxygen, sulphur or nitrogen, R⁴ is hydrogen or formamido, R⁵ is hydrogen, C1-6 alkyl, substituted alkyl, aryl or aralkyl, R⁶ and R⁷ are the same or different and represent hydrogen, C1-6 alkyl, substituted alkyl, halogen, amino, phenyl, substituted phenyl, hydroxy or C1-6 alkoxy or R⁶ and R⁷ form the residue of an optionally substituted 5- or 6-­membered carbocyclic ring or a 5- or 6- membered heterocyclic ring containing up to three hetero atoms selected from oxygen, sulphur or nitrogen, and X represents or tautomers thereof wherein R⁸ and R⁹ are the same or different and each represents hydroxy, or protected hydroxy. The use of the compounds is disclosed together with processes for their preparation.

  抗菌剂的化学式为（I）或其在体内可水解的酯类或药学上可接受的盐：其中R³为苯基，取代苯基，环己烯基，环己二烯基或含有最多三个氧，硫或氮杂原子的可选取代的5-或6-成员杂环；R⁴为氢或甲酰胺基，R⁵为氢，C1-6烷基，取代的烷基，芳基或芳基烷基，R⁶和R⁷相同或不同，代表氢，C1-6烷基，取代的烷基，卤素，氨基，苯基，取代苯基，羟基或C1-6烷氧基，或R⁶和R⁷形成可选取代的5-或6-成员碳环或含有最多三个氧，硫或氮杂原子的5-或6-成员杂环的残基，X代表 或其互变异构体，其中R⁸和R⁹相同或不同，每个代表羟基或保护羟基。公开了这些化合物的用途以及制备它们的过程。
• 2-Oxo-1-(((substituted sulfonyl)amino)carbonyl)azetidines
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0062876A1

  公开（公告）日：1982-10-20

  Antibacterial activity is exhibited by β-lactams having a substituent in the 1-position and an acylamino substituent in the 3-position wherein Z is oxygen or sulfur and R is alkyl, alkenyl, alkynyl, substituted alkyl, phenyl, substituted phenyl, a 5,6 or 7-membered heterocycle (Rc), phenylalkyl. (substituted-phenyl)alkyl, Rc-alkyl or-NR,Rb wherein R. and Rb are the same or different and each is hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl, phenylalkyl, (substituted phenyl)alkyl or one of R, and Rb is hydrogen, alkyl, phenyl, substituted phenyl, phenylalkyl or (substituted phenyl)alkyl and the other is amino (-NH2), alkanoylamino, arylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkylamino, dialkylamino, phenylamino, (substituted phenyl)- amino, hydroxy, cyano (-C=N), alkoxy, phenyloxy, (substituted phenyl)oxy, phenylalkoxy, (substituted phenyl)alkoxy, Rc as defined, above Rc-alkyl, Rc-alkoxy, alkylsulfonyl, alkylmethyleneamino, (alkyl-CH=N-), pheny-Imethyleneamino or (substituted phenyl)methyleneamino.

  具有以下特征的 β-内酰胺具有抗菌活性 其中 Z 是氧或硫，R 是烷基、烯基、炔基、取代烷基、苯基、取代苯基、5、6 或 7 元杂环 (Rc)、苯基烷基、(取代苯基)烷基、Rc-烷基或-NR,Rb。(取代苯基）烷基、Rc-烷基或-NR,Rb 其中 R.和 Rb 相同或不同，且各自为氢、烷基、取代的烷基、苯基、取代的苯基、苯基烷基、（取代的苯基）烷基或 R，和 Rb 中的一个为氢、烷基、苯基、取代的苯基、苯基烷基或（取代的苯基）烷基，另一个为氨基 (-NH2)、烷酰氨基、芳基羰基氨基、烷氧基羰基氨基、烷基磺酰基氨基、烷氧基羰基氨基、烷氧基羰基氨基、烷基磺酰胺、烷基酰胺、二烷基酰胺、苯基酰胺、（取代的苯基）-氨基、羟基、氰基（-C=N）、烷氧基、苯氧基、（取代的苯基）氧基、苯基烷氧基、（取代的苯基）烷氧基、如上定义的 Rc-烷基、Rc-烷氧基、烷基磺酰基、烷基亚甲基酰胺、（烷基-CH=N-）、苯基亚甲基酰胺或（取代的苯基）亚甲基酰胺。
• 4-Ether derivatives of 2-azetidinone-1-sulfonic acids
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0076758A2

  公开（公告）日：1983-04-13

  Antibacterial activity is exhibited by β-lactams having the formula wherein R is hydrogen or methoxy; R1 is acyl; R2 is alkyl, arylalkyl, carboxyalkyl, alkoxycarbonylalkyl, NH2-(CH2)n-, HO-(CH2)n- or aryl, wherein n is 2, 3 or 4; and M8 is hydrogen or a cation; with the proviso that if M⊕ is hydrogen the R1 or R2 group contains a basic function.

  β-内酰胺具有抗菌活性，其式为 其中 R 为氢或甲氧基； R1 是酰基 R2 是烷基、芳烷基、羧基、烷氧基羰基烷基、NH2-(CH2)n-、HO-( )n- 或芳基，其中 n 是 2、3 或 4；以及 M8 是氢或阳离子； 但如果 M⊕ 是氢，则 R1 或 R2 基团含有碱基官能团。
• NOVEL CEPHEM COMPOUND HAVING CATECHOL OR PSEUDO-CATECHOL STRUCTURE
  申请人：Shionogi & Co., Ltd.

  公开号：EP2703406A1

  公开（公告）日：2014-03-05

  The present invention provides a novel compound which has a wide antimicrobial spectrum, and in particular exhibits potent antimicrobial activity against beta-lactamase producing Gram negative bacteria. Specifically, the present invention provides a compound of the formula (I): wherein each symbol is as defined in the specification, or an amino-protected compound when the amino group is present on the ring in the 7-side chain, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same.

  本发明提供了一种新型化合物，它具有广泛的抗菌谱，特别是对β-内酰胺酶产生的革兰氏阴性菌具有强效抗菌活性。具体地说，本发明提供了一种式（I）化合物： 其中各符号如说明书中所定义、 或当氨基存在于 7 侧链的环上时的氨基保护化合物，或其药学上可接受的盐，以及由其组成的药物组合物。