3-氨基四氢噻吩-3-羧酸 | 32418-99-8

• 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
• 中文名称: 3-氨基四氢噻吩-3-羧酸
• 中文别名: 3-氨基-四氢-噻吩-3-甲酸
• 英文名称: 3-aminotetrahydrothiophene-3-carboxylic acid
• 英文别名: 3-Amino-3-(tetrahydrothienyl)carbonsaeure；3-Aminotetrahydrothienyl-3-carbonsaeure；3-azaniumylthiolane-3-carboxylate
• CAS: 32418-99-8
• 化学式: C₅H₉NO₂S
• mdl: MFCD01318281
• 分子量: 147.198
• InChiKey: SAKWWHXZZFRWCN-UHFFFAOYSA-N

物化性质

• 沸点：
  325.7±42.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氨基四氢噻吩-3-羧酸 在 4-二甲氨基吡啶 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 192.0h， 生成 (R)-3-(benzyloxycarbonylamino)tetrahydrothiophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids

  摘要：

  A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At(5)c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At(5)c (+/-)-3 in excellent yield. Diastereomeric esters derived from Cbz-At(5)c (+/-)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.010
• 作为产物：
  描述：

  7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione 在 barium dihydroxide 、 sodium hydroxide 、 Alcalase 、 水 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 32.0h， 生成 3-氨基四氢噻吩-3-羧酸
  参考文献：
  名称：

  A new series of cyclic amino acids as inhibitors of S-adenosyl L-methionine synthetase

  摘要：

  Optically active 3-amino-3-(tetrahydrofuranyl) carboxylic acid, 3-amino-3 -(tetrahydrothienyl) carboxylic acid and their corresponding six membered ring analogues have been synthesised and examined as potential inhibitors of the enzyme S-adenosylmethionine (AdoMet) synthetase.The kinetic behaviour of these compounds was studied using recombinant rat liver AdoMet synthetase (alpha-isoform) fractionated from E. coli transformed with the plasmid pSSRL-T7N. All the compounds tested were competitive inhibitors of the enzyme with respect to L-methionine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00267-4

文献信息

• Sulfonylanaloge Spirohydantoine
  作者：B. Unterhalt、A. Scheppan

  DOI：10.3797/scipharm.aut-01-198

  日期：——

  New thiasubstituted sulfonyl analogues of spirohydantoins were synthesized and tested for their anticonvulsant effects. In low concentrations they had no anticonvulsant activities, in higher ones they were neurotoxic.

  新的取代磺酰基螺内酰尿素类似物被合成并测试其抗惊厥效果。在低浓度下，它们没有抗惊厥活性，在较高浓度下，它们具有神经毒性。
• A new series of cyclic amino acids as inhibitors of S-adenosyl L-methionine synthetase
  作者：Karine Lavrador、Danielle Guillerm、Georges Guillerm

  DOI：10.1016/s0960-894x(98)00267-4

  日期：1998.7

  Optically active 3-amino-3-(tetrahydrofuranyl) carboxylic acid, 3-amino-3 -(tetrahydrothienyl) carboxylic acid and their corresponding six membered ring analogues have been synthesised and examined as potential inhibitors of the enzyme S-adenosylmethionine (AdoMet) synthetase.The kinetic behaviour of these compounds was studied using recombinant rat liver AdoMet synthetase (alpha-isoform) fractionated from E. coli transformed with the plasmid pSSRL-T7N. All the compounds tested were competitive inhibitors of the enzyme with respect to L-methionine. (C) 1998 Elsevier Science Ltd. All rights reserved.
• MORIMOTO, YOSHIHISA;ACHIWA, KAZUO, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3845-3849
  作者：MORIMOTO, YOSHIHISA、ACHIWA, KAZUO

  DOI：——

  日期：——
• [EN] NOVEL DPP1 INHIBITORS AND USES THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DE DPP1 ET LEURS UTILISATIONS
  申请人：[en]INSMED INCORPORATED

  公开号：WO2024026433A2

  公开（公告）日：2024-02-01

  Provided herein are novel DPP1 inhibitor compounds having the general structure of Formula (I), (II) or (III), or a pharmaceutically acceptable salt thereof. Also provided are certain methods of treatment, e.g., a method for treating an obstructive disease of the airway or a method of treating an inflammatory condition with a composition comprising an effective amount of one of the compounds provided herein.
• Synthesis of Sterically Hindered <i>N</i>-Acylated Amino Acids from <i>N</i>-Carboxyanhydrides
  作者：Gabriel Schäfer、Jeffrey W. Bode

  DOI：10.1021/ol500523n

  日期：2014.3.7

  Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.