4-amino-5-chlorothiophene-2-carboxylic acid | 89499-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-amino-5-chlorothiophene-2-carboxylic acid
• 英文别名: 2-Thiophenecarboxylic acid, 4-amino-5-chloro-
• CAS: 89499-41-2
• 化学式: C₅H₄ClNO₂S
• 分子量: 177.611
• InChiKey: AZXFRUSWZQOXLB-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  408.6±45.0 °C(Predicted)
• 密度：
  1.680±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[4-[(5S)-5-(氨甲基)-2-羰基-3-唑烷基]苯基]-3-吗啡啉酮 、 4-amino-5-chlorothiophene-2-carboxylic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-Amino-5-chloro-thiophene-2-carboxylic acid {(S)-2-oxo-3-[4-(3-oxo-morpholin-4-yl)-phenyl]-oxazolidin-5-ylmethyl}-amide
  参考文献：
  名称：

  Discovery of the Novel Antithrombotic Agent 5-Chloro-N-({(5S)-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene- 2-carboxamide (BAY 59-7939):  An Oral, Direct Factor Xa Inhibitor

  摘要：

  Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the identification of small-molecule inhibitors with good oral bioavailability. We identified oxazolidinone derivatives as a new class of potent FXa inhibitors. Lead optimization led to the discovery of BAY 59-7939 (5), a highly potent and selective, direct FXa inhibitor with excellent in vivo antithrombotic activity. The X-ray crystal structure of 5 in complex with human FXa clarified the binding mode and the stringent requirements for high affinity. The interaction of the neutral ligand chlorothiophene in the S1 subsite allows for the combination of good oral bioavailability and high potency for nonbasic 5. Compound 5 is currently under clinical development for the prevention and treatment of thromboembolic diseases.

  DOI：

  10.1021/jm050101d
• 作为产物：
  描述：

  4-氨基-5-氯噻吩-2-羧酸盐酸盐 、 碳酸氢钠 以89%的产率得到
  参考文献：
  名称：

  GOLDFARB, YA. L.;BULGAKOVA, V. N.;FABRICHNYJ, B. P., XIMIYA GETEROTSIKL. SOEDIN., 1983, N 12, 1626-1629

  摘要：

  DOI：

文献信息

• INSECTICIDAL COMPOUNDS
  申请人：Jung Pierre

  公开号：US20090192175A1

  公开（公告）日：2009-07-30

  Novel heteroaromatic compounds of formula (I): wherein A 1 , A 2 , A 3 , R 1 , R 2 , G 1 , G 2 , Q 1 and Q 2 are as defined in claim 1 ; or salts or N-oxides thereof. Furthermore, the present invention relates to processes for preparing compounds of formula (I), to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.

  式(I)的新异杂芳化合物：其中A1、A2、A3、R1、R2、G1、G2、Q1和Q2如权利要求1所定义；或其盐或N-氧化物。此外，本发明涉及制备式(I)化合物的方法，以及包含它们的杀虫剂、杀螨剂、杀软体动物剂和杀线虫剂组合物，以及使用它们来打击和控制昆虫、螨、软体动物和线虫害的方法。
• Reductive acetylation of nitrocarboxylic acids of the thiophene and furan series or their esters
  作者：Ya. L. Gol'dfarb、V. N. Bulgakova、B. P. Fabrichnyi

  DOI：10.1007/bf00842830

  日期：1983.12
• US8252936B2
  申请人：——

  公开号：US8252936B2

  公开（公告）日：2012-08-28
• [EN] INSECTICIDAL COMPOUNDS<br/>[FR] COMPOSÉS INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2007128410A1

  公开（公告）日：2007-11-15

  [EN] Novel heteroaromatic compounds of formula (I): wherein A¹, A², A³, R¹, R², G¹, G², Q¹ and Q² are as defined in claim 1; or salts or N-oxides thereof. Furthermore, the present invention relates to processes for preparing compounds of formula (I), to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
  [FR] L'invention porte sur de nouveaux composés hétéroaromatiques de formule (I) dans laquelle: A1, A2, A3, R1, R2, G1, G2, Q1 et Q2 sont tels que définis dans la revendication 1; ou sur leurs sels ou N oxydes. L'invention porte également: sur le procédé de préparation lesdits composés; sur des compositions insecticides, acaricidesl, molluscicides et nématicides les comprenant; et sur des leurs procédés d'utilisation pour combattre et éradiquer les insectes, les acariens, les mollusques et les nématodes nuisibles.
• Discovery of the Novel Antithrombotic Agent 5-Chloro-<i>N</i>-({(5<i>S</i>)-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene- 2-carboxamide (BAY 59-7939):  An Oral, Direct Factor Xa Inhibitor
  作者：Susanne Roehrig、Alexander Straub、Jens Pohlmann、Thomas Lampe、Josef Pernerstorfer、Karl-Heinz Schlemmer、Peter Reinemer、Elisabeth Perzborn

  DOI：10.1021/jm050101d

  日期：2005.9.1

  Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the identification of small-molecule inhibitors with good oral bioavailability. We identified oxazolidinone derivatives as a new class of potent FXa inhibitors. Lead optimization led to the discovery of BAY 59-7939 (5), a highly potent and selective, direct FXa inhibitor with excellent in vivo antithrombotic activity. The X-ray crystal structure of 5 in complex with human FXa clarified the binding mode and the stringent requirements for high affinity. The interaction of the neutral ligand chlorothiophene in the S1 subsite allows for the combination of good oral bioavailability and high potency for nonbasic 5. Compound 5 is currently under clinical development for the prevention and treatment of thromboembolic diseases.