3-thienylpyruvic acid | 13781-71-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-thienylpyruvic acid
• 英文别名: (thien-3-yl)pyruvic acid；2-Oxo-3-(thiophen-3-yl)propanoic acid；2-oxo-3-thiophen-3-ylpropanoic acid
• CAS: 13781-71-0
• 化学式: C₇H₆O₃S
• 分子量: 170.189
• InChiKey: QELZMQDJRPDHKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-thienylpyruvic acid 、 碘甲烷 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-Methyl-2-oxo-3-thiophen-3-yl-butyric acid
  参考文献：
  名称：

  Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

  摘要：

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.024
• 作为产物：
  描述：

  3-(3-噻吩)-L-丙氨酸 在 L-amino acid oxidase 、 catalase 作用下， 反应 4.0h， 以25%的产率得到3-thienylpyruvic acid
  参考文献：
  名称：

  Mechanism and Mechanism-Based Inactivation of 4-Hydroxyphenylpyruvate Dioxygenase

  摘要：

  Six substrate analogs of 4-hydroxyphenylpyruvate, specifically pentafluorophenylpyruvate, 4-hydroxytetrafluorophenylpyruvate,2-thienylpyruvate, 3-thienylpyruvate, thiophenol oxalate, and p-thiocresoloxalate were synthesized and their interactions with porcine liver 4-hydroxyphenylpyruvate dioxygenase investigated. Both pentafluorophenylpyruvate and thiophenol oxalate are competitive inhibitors of the enzyme with Ki values of 14 and 150 mu M, respectively, but p-thiocresol oxalate has no effect on the enzymic activity. The other three substrate analogs are both substrates and mechanism-based inactivators of the enzyme with the following kinetic characteristics (compound, K-m, V-max, k(mact), K', partition ratio) at pH 6.0, 37 degrees C, and an air atmosphere: 4-hydroxytetrafluorophenylpyruvate, 50 mu M, 1.9 mkat/ kg, 1.5/min, 70 mu M 4.2; 2-thienylpyruvate, 500 mu M, 7.8 mkat/kg, 0.6/min, 400 CLM, 41; 3thienylpymvate, 250 mu M, 2 9 mkatikg, 0.6/min, 300 CLM, 22. When inactivated, the dioxygenase was found to contain per mole of active enzyme, 0.78 mol of label from 3-thienyt3 [3H]pyruvate and 0.85 mol of label from 4-hydroxytetrafluorophenyl-3 [3H]pyruvate. The product formed from the enzyme-catalyzed oxidation of 3-thienylpyruvate was determined to be 3-carboxymethyl-3-thiolene-2-one. The implication of these results to the mechanism of the dioxygenase is considered, (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1028

文献信息

• Process for preparing benzoperhydroisoindole compounds
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US06291679B1

  公开（公告）日：2001-09-18

  The present invention relates to a novel process for the preparation of benzoperhydroisindole compounds.

  本发明涉及一种用于制备苯丙内酰环己烷化合物的新工艺。
• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。
• SYNTHESIS METHOD FOR L-HETEROCYCLIC AMINO ACID AND PHARMACEUTICAL COMPOSITION HAVING THEREOF
  申请人：ASYMCHEM LABORATORIES (TIANJIN) CO., LTD

  公开号：US20160153015A1

  公开（公告）日：2016-06-02

  A synthesis method for an L-heterocyclic amino acid and a pharmaceutical composition having the said amino acid are provided in the present disclosure. The synthesis method comprises: step A: preparing a heterocyclic keto acid, wherein the heterocycle in the heterocyclic keto acid is selected from any one of a five-membered heterocycle, a six-membered heterocycle, a seven-membered heterocycle, an alkyl-substituted five-membered heterocycle, an alkyl-substituted six-membered heterocycle, and an alkyl-substituted seven-membered heterocycle, and the keto acid group in the heterocyclic keto acid has a structural formula of and is located on any one of the carbon positions of the heterocycle, and step B: mixing the heterocyclic keto acid with ammonium formate, a phenylalanine dehydrogenase, a formate dehydrogenase and a coenzyme NAD + , and carrying out a reductive amination reaction to generate L-heterocyclic amino acid, wherein the amino acid sequence of the phenylalanine dehydrogenase is SEQ ID No. 1.

  本公开提供了一种L-杂环氨基酸的合成方法和具有该氨基酸的制药组合物。该合成方法包括：步骤A：制备杂环酮酸，其中杂环在杂环酮酸中选自五元杂环、六元杂环、七元杂环、烷基取代的五元杂环、烷基取代的六元杂环和烷基取代的七元杂环，而杂环酮酸中的酮酸基具有结构式，位于杂环的任一碳位上；步骤B：将杂环酮酸与甲酸铵、苯丙氨酸脱氢酶、甲酸脱氢酶和辅酶NAD+混合，并进行还原胺化反应以生成L-杂环氨基酸，其中苯丙氨酸脱氢酶的氨基酸序列为SEQ ID No. 1。
• Beta-lactam antibacterial agents, their pharmaceutical compositions and process for their preparation
  申请人：BEECHAM GROUP PLC

  公开号：EP0004134A1

  公开（公告）日：1979-09-19

  The compounds of the formula (I): wherein R1 is a hydrogen atom, a trityl group or an acyl group as found in known antibacterially active penicillins or cephalosporins; R2 is a hydrogen atom, a lower alkyl group or an aryl group; R3 is a hydrogen atom, a lower alkyl group, a substituted lower alkyl or a thiosubstituted lower alkyl group; and R4 is a group such that COzR4 is a carboxylic acid group or a salt or readily removable ester thereof; are antibiotics. The compounds may be formulated in pharmaceutical compositions. Processes for the preparation of the compounds (I) are also described.

  式(I)化合物： 其中 R1 是氢原子、三烷基或酰基，如已知的具有抗菌活性的青霉素或头孢菌素中的酰基；R2 是氢原子、低级烷基或芳基；R3 是氢原子、低级烷基、取代的低级烷基或硫代低级烷基；R4 是一个基团，使得 COzR4 是一个羧酸基团或其盐或易去除的酯；这些化合物是抗生素。这些化合物可配制成药物组合物。 还描述了制备化合物(I)的工艺。
• Beta-lactam antibacterial agents
  申请人：BEECHAM GROUP PLC

  公开号：EP0048096A1

  公开（公告）日：1982-03-24

  A compound of formula (I) or a salt thereof: wherein R' is an amino group, an azido group, or an acylamino group as found in antibacterially active penicillins or cephalosporins; R2 is a hydrogen atom or a C1-4 alkyl group; R3 is a hydrogen atom, or a C1-4 alkyl group optionally substituted by a carboxyl, carboxylic ester, hydroxy, C1-4 alkyloxy, acyloxy or heterocyclylthio group; and R4 is hydrogen or a readily removable carboxyl protecting group. The compounds wherein R1 is an acylamino group are found in known antibacterially active penicillins and cephalosporins and wherein R4 is a hydrogen, a pharmaceutically acceptable salting ion or an in vivo hydrolysable ester forming radical may be formulated in pharmaceutical compositions. Processes for the preparation of the compound (I) are also described.

  式 (I) 的化合物或其盐： 其中 R' 是氨基、叠氮基或酰氨基，如抗菌活性青霉素或头孢菌素中的酰氨基； R2 是氢原子或 C1-4 烷基； R3 是氢原子或任选被羧基、羧酸酯、羟基、C1-4 烷氧基、酰氧基或杂环硫基取代的 C1-4 烷基；以及 R4 是氢或易于去除的羧基保护基团。 R1为酰氨基的化合物存在于已知的具有抗菌活性的青霉素和头孢菌素中，R4为氢、药学上可接受的盐离子或体内可水解的酯形成基的化合物可配制成药物组合物。 此外，还描述了制备化合物 (I) 的工艺。