3-(4-chlorobenzenesulfonylamino)thiophene-2-carboxylic acid | 254878-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorobenzenesulfonylamino)thiophene-2-carboxylic acid
• 英文别名: 3-(4-Chloro-phenylsulfonylamino)-thiophene-2-carboxylic acid；3-{[(4-Chlorophenyl)sulfonyl]amino}thiophene-2-carboxylic acid；3-[(4-chlorophenyl)sulfonylamino]thiophene-2-carboxylic acid
• CAS: 254878-28-9
• 化学式: C₁₁H₈ClNO₄S₂
• mdl: MFCD12558701
• 分子量: 317.774
• InChiKey: KFSMKLIYYYGIKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobenzenesulfonylamino)thiophene-2-carboxylic acid 在 五氯化磷 作用下， 生成 3-(4-Chloro-phenylsulfonylamino)-thiophene-2-carboxylic acid chloride
  参考文献：
  名称：

  Sulfur substituted sulfonylaminocarboxylic acid N-arylamides, their preparation, their use and pharmaceutical preparations comprising them

  摘要：

  本发明涉及以下式I的化合物，其中A1、A2、R1、R2、R3、X和n如权利要求中所定义，这些化合物是有价值的药用活性化合物，可用于治疗和预防疾病，例如心血管疾病，如高血压、心绞痛、心力衰竭、血栓形成或动脉粥样硬化。式I的化合物能够调节体内环鸟苷酸单磷酸（cGMP）的产生，并且通常适用于治疗和预防与破坏cGMP平衡有关的疾病。此外，本发明还涉及制备式I化合物的方法，它们用于治疗和预防上述疾病以及用于制备用途的药物，以及包含式I化合物的药物制剂。

  公开号：

  US06335334B1
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 吡啶 、 sodium hydroxide 作用下， 反应 25.0h， 生成 3-(4-chlorobenzenesulfonylamino)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Structure-Based Optimization of a Non-β-lactam Lead Results in Inhibitors That Do Not Up-Regulate β-Lactamase Expression in Cell Culture

  摘要：

  Bacterial expression of beta-lactamases is the most widespread resistance mechanism to beta-lactam antibiotics, such as penicillins and cephalosporins. There is a pressing need for novel, non-beta-lactam inhibitors of these enzymes. One previously discovered novel inhibitor of the beta-lactamase AmpC, compound 1, has several favorable properties: it is chemically dissimilar to beta-lactams and is a noncovalent, competitive inhibitor of the enzyme. However, at 26 microM its activity is modest. Using the X-ray structure of the AmpC/1 complex as a template, 14 analogues were designed and synthesized. The most active of these, compound 10, had a K(i) of 1 microM, 26-fold better than the lead. To understand the origins of this improved activity, the structures of AmpC in complex with compound 10 and an analogue, compound 11, were determined by X-ray crystallography to 1.97 and 1.96 A, respectively. Compound 10 was active in cell culture, reversing resistance to the third generation cephalosporin ceftazidime in bacterial pathogens expressing AmpC. In contrast to beta-lactam-based inhibitors clavulanate and cefoxitin, compound 10 did not up-regulate beta-lactamase expression in cell culture but simply inhibited the enzyme expressed by the resistant bacteria. Its escape from this resistance mechanism derives from its dissimilarity to beta-lactam antibiotics.

  DOI：

  10.1021/ja042984o

文献信息

• [EN] SULFUR SUBSTITUTED SULFONYLAMINOCARBOXYLIC ACID N-ARYLAMIDES, THEIR PREPARATION, THEIR USE AND PHARMACEUTICAL PREPARATIONS COMPRISING THEM<br/>[FR] N-ARYLAMIDES D'ACIDE SULFONYLAMINOCARBOXYLIQUE A SUBSTITUTION SOUFRE, PREPARATION ET UTILISATION DE CES DERNIERS, PREPARATIONS PHARMACEUTIQUES CONTENANT CES COMPOSES
  申请人：HOECHST MARION ROUSSEL DE GMBH

  公开号：WO2000002851A1

  公开（公告）日：2000-01-20

  The present invention relates to compounds of formula (I), wherein A?1, A2, R1, R2, R3¿, X and n are as defined in the claims, which are valuable pharmaceutically active compounds for the therapy and prophylaxis of diseases, for example of cardiovascular diseases such as hypertension, angina pectoris, cardiac insufficiency, thromboses or atherosclerosis. The compounds of formula (I) are capable of modulating the body's production of cyclic guanosine monophosphate (cGMP) and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of formula (I), to their use for the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of formula (I).

  本发明涉及式（I）化合物，其中A1，A2，R1，R2，R3，X和n如权利要求所定义，这些化合物是有价值的药物活性化合物，用于治疗和预防疾病，例如心血管疾病，如高血压，心绞痛，心力衰竭，血栓或动脉硬化。式（I）化合物能够调节体内环磷鸟苷酸（cGMP）的产生，并且通常适用于治疗和预防与cGMP平衡紊乱有关的疾病。本发明还涉及制备式（I）化合物的方法，它们用于治疗和预防上述疾病以及制备药物，以及包含式（I）化合物的制药制剂。
• SULFUR SUBSTITUTED SULFONYLAMINOCARBOXYLIC ACID N-ARYLAMIDES, THEIR PREPARATION, THEIR USE AND PHARMACEUTICAL PREPARATIONS COMPRISING THEM
  申请人：SCHINDLER Ursula

  公开号：US20120108573A1

  公开（公告）日：2012-05-03

  The present invention relates to compounds of the formula I wherein A 1 , A 2 , R 1 , R 3 , X and n are as defined in the claims, which are valuable pharmaceutically active compounds for the therapy and prophylaxis of diseases, for example of cardiovascular diseases such as hypertension, angina pectoris, cardiac insufficiency, thromboses or atherosclerosis. The compounds of the formula fare capable of modulating the body's production of cyclic guanosine monophosphate (cGMP) and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of the formula I, to their use for the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of the formula I.

  本发明涉及公式I的化合物，其中A1、A2、R1、R3、X和n如权利要求中所定义，这些化合物是有价值的药物活性化合物，用于治疗和预防疾病，例如心血管疾病，如高血压、心绞痛、心力衰竭、血栓或动脉硬化。公式F的化合物能够调节体内环磷酸鸟苷单磷酸（cGMP）的产生，通常适用于治疗和预防与扰乱cGMP平衡有关的疾病。本发明还涉及制备公式I化合物的方法，以及它们用于治疗和预防上述疾病和制备药物的用途，以及包含公式I化合物的制药制剂。
• Sulfur substituted sulfonylaminocarboxylic acid N-heteroarylamides, their preparation, their use and pharmaceutical preparations comprising them
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：EP1614678A2

  公开（公告）日：2006-01-11

  The present invention relates to compounds of the formula I wherein A1, A2, R1, R2, R3, X and n are as defined in the claims, which are valuable pharmaceutically active compounds for the therapy and prophylaxis of diseases, for example of cardiovascular diseases such as hypertension, angina pectoris, cardiac insufficiency, thromboses or atherosclerosis. The compounds of the formula I are capable of modulating the body's production of cyclic guanosine monophosphate (cGMP) and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of the formula I, to their use for the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of the formula I.

  本发明涉及式 I 的化合物 其中 A1、A2、R1、R2、R3、X 和 n 如权利要求书中所定义，是治疗和预防疾病（例如高血压、心绞痛、心功能不全、血栓或动脉粥样硬化等心血管疾病）的有价值的药物活性化合物。式 I 的化合物能够调节体内环磷酸鸟苷（cGMP）的生成，通常适用于治疗和预防与 cGMP 平衡失调有关的疾病。此外，本发明还涉及式 I 化合物的制备工艺、其在治疗和预防上述疾病中的用途以及为此目的制备药物的工艺，以及包含式 I 化合物的药物制剂。
• US6335334B1
  申请人：——

  公开号：US6335334B1

  公开（公告）日：2002-01-01
• US6881735B2
  申请人：——

  公开号：US6881735B2

  公开（公告）日：2005-04-19