Methyl 2-oxo-2-(3-benzothienyl)acetate | 195070-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: Methyl 2-oxo-2-(3-benzothienyl)acetate
• 英文别名: methyl 2-(1-benzothiophen-3-yl)-2-oxoacetate
• CAS: 195070-91-8
• 化学式: C₁₁H₈O₃S
• 分子量: 220.249
• InChiKey: VLPJNVBYSDVPMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-[3-(2-amino-2-oxoethyl)indol-1-yl]propyl]carbamate 、 Methyl 2-oxo-2-(3-benzothienyl)acetate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[3-[3-[4-(1-benzothiophen-3-yl)-2,5-dioxopyrrol-3-yl]indol-1-yl]propyl]carbamate
  参考文献：
  名称：

  Aryl–indolyl maleimides as inhibitors of CaMKIIδ. Part 1: SAR of the aryl region

  摘要：

  A family of aryl-substituted maleimides was prepared and studied for their activity against calmodulin dependant kinase. Inhibitory activities against the enzyme ranged from 34 nM to > 20 mu M and were dependant upon both the nature of the aryl group and the hydrogen bond donating potential of the maleimide ring. Key interactions with the kinase ATP site and hinge region were found to be consistent with homology modeling predictions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.059

文献信息

• .beta.-thiopropionyl-aminoacid derivatives and their use as
  申请人：SmithKline Beecham p.l.c.

  公开号：US06048852A1

  公开（公告）日：2000-04-11

  A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a .beta.-lactam antibiotic, a therapeutically effective amount of an amino acid derivative of Formula (I) or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, ##STR1## wherein: R is hydrogen, a salt forming cation or an in vivo hydrolysable ester-forming group; R.sub.1 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms or by a mercapto, (C.sub.1-6)alkoxy, hydroxy, amino, nitro, carboxy, (C.sub.1-6)alkylcarbonyloxy, (C.sub.1-6)alkoxycarbonyl, formyl or (C.sub.1-6)alkylcarbonyl group, (C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl(C.sub.1-6)alkyl, heterocyclyl or heterocyclyl(C.sub.1-6)alkyl; R.sub.2 is hydrogen, (C.sub.1-6)alkyl or aryl(C.sub.1-6)alkyl; R.sub.3 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms, (C.sub.3-7)cycloalkyl, fused aryl(C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, heterocyclyl or heterocyclyl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, where m is 0 to 3, n is 1 to 3, each R.sub.10 and R.sub.11 is independently hydrogen or (C.sub.1-4)alkyl and X is O, S(O).sub.x where x is 0-2, or a bond; R.sub.4 is hydrogen, or an in vivo hydrolysable acyl group; and R.sub.5 and R.sub.6 are independently hydrogen and (C.sub.1-6)alkyl or together represent (CH.sub.2).sub.p where p is 2 to 5. Some compounds are claimed per se.

  一种治疗人类或动物细菌感染的方法，包括与β-内酰胺类抗生素联合使用，治疗有效量的式（I）的氨基酸衍生物或其药学上可接受的盐，溶剂或体内可水解酯，其中：R为氢，形成盐的阳离子或体内可水解的酯形成基；R1为氢，（C1-6）烷基，可选地被最多三个卤素原子或硫巴替氧基，（C1-6）烷氧基，羟基，氨基，硝基，羧基，（C1-6）烷基羰氧基，（C1-6）烷氧羰基，甲酰基或（C1-6）烷基羰基基，（C3-7）环烷基，（C3-7）环烷基（C2-6）烷基，（C2-6）烯基，（C2-6）炔基，芳基，芳基（C1-6）烷基，杂环烷基或杂环烷基（C1-6）烷基；R2为氢，（C1-6）烷基或芳基（C1-6）烷基；R3为氢，（C1-6）烷基，可选地被最多三个卤素原子取代，（C3-7）环烷基，融合的芳基（C3-7）环烷基，（C3-7）环烷基（C2-6）烷基，（C2-6）烯基，（C2-6）炔基，芳基，芳基-(CHR10)m-X-(CHR11)n，杂环烷基或杂环烷基-(CHR10)m-X-(CHR11)n，其中m为0至3，n为1至3，每个R10和R11独立地为氢或（C1-4）烷基，X为O，S（O）x，其中x为0-2，或键；R4为氢，或体内可水解的酰基；R5和R6独立地为氢和（C1-6）烷基，或一起表示（CH2）p，其中p为2至5。其中一些化合物本身也被要求。
• BETA-THIOPROPIONYL-AMINOACID DERIVATIVES AND THEIR USE AS BETA-LACTAMASE INHIBITORS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0900197A1

  公开（公告）日：1999-03-10
• US6048852A
  申请人：——

  公开号：US6048852A

  公开（公告）日：2000-04-11
• [EN] BETA-THIOPROPIONYL-AMINOACID DERIVATIVES AND THEIR USE AS BETA-LACTAMASE INHIBITORS<br/>[FR] DERIVES D'ACIDES BETA-THIOPROPIONYLE AMINES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE BETA-LACTAMASE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1997030027A1

  公开（公告）日：1997-08-21

  (EN) A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a $g(b)-lactam antibiotic, a therapeutically effective amount of an amino acid derivative of Formula (I) or a pharmaceutically acceptable salt, solvate or $i(in vivo) hydrolysable ester thereof, wherein: R is hydrogen, a salt forming cation or an $i(in vivo) hydrolysable ester-forming group; R1 is hydrogen, (C1-6)alkyl optionally substituted by up to three halogen atoms or by a mercapto, (C1-6)alkoxy, hydroxy, amino, nitro, carboxy, (C1-6)alkylcarbonyloxy, (C1-6)alkoxycarbonyl, formyl or (C1-6)alkylcarbonyl group, (C3-7)cycloalkyl, (C3-7)cycloalkyl(C2-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, aryl, aryl(C1-6)alkyl, heterocyclyl or heterocyclyl(C1-6)alkyl; R2 is hydrogen, (C1-6)alkyl or aryl(C1-6)alkyl; R3 is hydrogen, (C1-6)alkyl optionally substituted by up to three halogen atoms, (C3-7)cycloalkyl, fused aryl(C3-7)cycloalkyl, (C3-7)cycloalkyl(C2-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, aryl, aryl-(CHR10)m-X-(CHR11)n, heterocyclyl or heterocyclyl-(CHR10)m-X-(CHR11)n, where m is 0 to 3, n is 1 to 3, each R10 and R11 is independently hydrogen or (C1-4)alkyl and X is O, S(O)x where x is 0-2, or a bond; R4 is hydrogen, or an $i(in vivo) hydrolysable acyl group; and R5 and R6 are independently hydrogen and (C1-6)alkyl or together represent (CH2)p where p is 2 to 5. Some compounds are claimed per se.(FR) Procédé de traitement d'infections bactériennes chez l'homme ou chez l'animal, consistant à administrer, combiné à un antibiotique de $g(b)-lactame, une quantité efficace sur le plan thérapeutique d'un dérivé d'acide aminé de Formule (I) ou d'un de ses sels, solvates ou esters hydrolysables $i(in vivo), acceptables sur le plan pharmaceutique, formule dans laquelle R représente hydrogène, un cation formant un sel ou un groupe formant un ester hydrolysable in vivo; R1 représente hydrogène, alkyle C1-C6 éventuellement substitué par trois atomes d'halogène au maximum ou par un groupe mercapto, alcoxy C1-C6,hydroxy, amino, nitro, carboxy, alkylcarbonyloxy C1-C6, alcoxycarbonyle C1-C6, formyle ou alkylcarbonyle C1-C6, cycloalkyle C3-C7, cycloalkyle C3-C7 alkyle C2-C6, alkényle C2-C6, alkynyle C2-C6, aryle, arylalkyle C1-C6, hétérocyclyle ou hétérocyclyle alkyle C1-C6; R2 représente hydrogène, alkyle C1-C6 ou aryle alkyle C1-C6; R3 représente hydrogène, alkyle C1-C6 éventuellement substitué par trois atomes d'halogène au maximum, cycloalkyle C3-C7, aryl fusionné cycoalkyle C3-C7, cycloalkyle C3-C7 alkyle C2-C6, alkényle C2-C6, alkynyle C2-C6, aryle-(CHR10)m-X-(CHR11)n, hétérocyclyle ou hétérocyclyle-(CHR10)m-X (CHR11)n dans laquelle m est 0 à 3, n est 1 à 3, chaque R10 et R11 représente indépendamment hydrogène ou alkyle C1-C4 et X représente 0-2 ou une liaison; R4 représente hydrogène ou un groupe acyle hydrolysable $i(in vivo); R5 et R6 représentent indépendamment hydrogène et alkyle C1-C6 ou représentent ensemble (CH2)n dans laquelle p est 2 à 5. On revendique certains composés.