5-(4-chlorophenyl)thiophene-2-sulfonyl chloride | 209592-43-8

• 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: 5-(4-chlorophenyl)thiophene-2-sulfonyl chloride
• 英文别名: 5-(4-chlorophenyl)thiophene-2-sulphonyl chloride；5-(4-Chlorophenyl)-2-thiophenesulfonyl chloride
• CAS: 209592-43-8
• 化学式: C₁₀H₆Cl₂O₂S₂
• 分子量: 293.194
• InChiKey: OFXSPNQQRVXCDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)thiophene-2-sulfonyl chloride 在 吡啶 、 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 5-(4-chloro-phenyl)-thiophene-2-sulfonic acid (2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amide
  参考文献：
  名称：

  Studies towards the identification of a new generation of atypical antipsychotic agents

  摘要：

  A rational structure-activity relationship study around compound (1) is reported. The lead optimisation programme led to the identification of sulfonamide (25), a molecule combining dopamine D-2/D-3 receptor antagonism with serotonin 5-HT2A, 5-HT2C, 5-HT6 receptor antagonism for an effective treatment of schizophrenia. Compound (25) was shown to possess the required in vivo activity with no EPS liability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.036
• 作为产物：
  描述：

  5-(4-Chlorophenyl)thiophene-2-sulfonic acid 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-(4-chlorophenyl)thiophene-2-sulfonyl chloride
  参考文献：
  名称：

  Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors

  摘要：

  A series of 1-sulfonylaminocyclopropanecarboxylates was synthesized as ADAMTS-5 (Aggrecanase-2) inhibitors. After an intensive investigation of the central cyclopropane core including its absolute stereochemistry and substituents, we found compound 22 with an Agg-2 IC(50) = 7.4 nM, the most potent ADAMTS-5 inhibitor reported so far. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.093

文献信息

• [EN] N-SUBSTITUTED-N-SULFONYLAMINOCYCLOPROPANE COMPOUNDS AND PHARMACEUTICAL USE THEREOF<br/>[FR] COMPOSES DE N-SULFONYLAMINOCYCLOPROPANE N-SUBSTITUE ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：JAPAN TOBACCO INC

  公开号：WO2005058808A1

  公开（公告）日：2005-06-30

  The present invention provides a compound having aggrecanase inhibitory activity and MMP-13 inhibitory activity, and useful as a therapeutic agent for osteoarthritis, rheumatoid arthritis and the like, more specifically, a N-substituted-N-sulfonylaminocyclopropane compound of formula (1) : wherein R1 is -W-A1-W1-A2, W is (CH2)m-X-(CH2)n-, wherein W1 is -(CH2)m1-X1-(CH2)n1-, m, m1, n and n1 are the same or different and each is 0 to 6, X and X1 are the same or different and each is a single bond, etc., A1 is an optionally substituted C3-14 hydrocarbon ring group, etc. and A2 is a substituted C3-14 hydrocarbon ring group etc.; R2 is -(CH2)r-CO-R8, etc., wherein r is 0 to 6 and R8 is a C1-6 alkoxy group, etc.; R3 and R4 are the same or different and each is a hydrogen atom, a C1-6 alkyl group, etc.; and R5 is -CO2R21, etc.; R30 and R31 are the same or different and each is a hydrogen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有减少聚集素酶活性和MMP-13抑制活性的化合物，并且可用作治疗骨关节炎、类风湿性关节炎等疾病的治疗剂，更具体地说，是一种具有如下结构的N-取代-N-磺酰氨基环丙烷化合物（式1）：其中R1为-W-A1-W1-A2，W为(CH2)m-X-(CH2)n-，其中W1为-(CH2)m1-X1-(CH2)n1-，m、m1、n和n1相同或不同，且每个为0至6，X和X1相同或不同，且每个为单键，A1为可选择取代的C3-14碳氢环基团，等等，A2为取代的C3-14碳氢环基团等；R2为-(CH2)r-CO-R8，等等，其中r为0至6，R8为C1-6烷氧基团，等等；R3和R4相同或不同，每个为氢原子、C1-6烷基基团，等等；R5为-CO2R21，等等；R30和R31相同或不同，每个为氢原子，等等；或其前药或其药学上可接受的盐。
• [EN] PIPERAZINE COMPOUNDS AS INHIBITORS OF MMP OR TNF<br/>[FR] COMPOSES DE PIPERAZINE INHIBITEURS DE METALLOPROTEASE MATRICIELLE (MMP) OU DE TNF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1998027069A1

  公开（公告）日：1998-06-25

  (EN) A compound of formula (I) wherein A is a sulfonyl or a carbonyl; R1 is an optionally substituted aryl, an optionally substituted heterocyclic group, an optionally substituted lower alkyl or an optionally substituted lower alkenyl; R2 is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; R3 is an optionally substituted lower alkyl, an optionally substituted lower alkoxy, an optionally substituted aryloxy, an optionally substitued lower alkenyl, an optionally substituted aryl, an optionally substituted heterocyclic group or an optionally substitued amino; R4 is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; R5 is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; and R10 is a hydroxy or a protected hydroxy, and a pharmaceutically acceptable salt thereof. The compound of the present invention is useful as a medicament for prophylactic and therapeutic treatment of MMP- or TNF$g(a)-mediated diseases.(FR) Composé de la formule (I) dans laquelle A est un sulfuryle ou un carbonyle; R1 est un aryle éventuellement substitué, un groupe hétérocyclique éventuellement substitué, un alkyle inférieur éventuellement substitué ou un alcényle inférieur éventuellement substitué; R2 est un hydrogène, un alkyle inférieur éventuellement substitué, un aryle éventuellement substitué ou un groupe hétérocyclique éventuellement substitué; R3 est un alkyle inférieur éventuellement substitué, un alkoxy inférieur éventuellement substitué, un aryloxy éventuellement substitué, un alcényle inférieur éventuellement substitué, un aryle éventuellement substitué ou un amino éventuellement substitué; R4 est un hydrogène, un alkyle inférieur éventuellement substitué, un aryle éventuellement substitué ou un groupe hétérocyclique éventuellement substitué ou un groupe hétérocyclique éventuellement substitué, R5 est un hydrogène, un alkyle inférieur éventuellement substitué, un aryle éventuellement substitué ou un groupe hétérocyclique éventuellement substitué; et R10 est un hydroxy ou un hydroxy protégé, et un sel pharmaceutiquement acceptable de ce composé. Ce composé est utile comme médicament pour le traitement préventif et curatif des maladies induites par MMP ou TNF$g(a).

  化合物的化学式为(I)，其中A为磺酰基或羰基；R1为可选取代的芳基，可选取代的杂环基，可选取代的低碳基或可选取代的低碳烯基；R2为氢，可选取代的低碳基，可选取代的芳基或可选取代的杂环基；R3为可选取代的低碳基，可选取代的低碳氧基，可选取代的芳氧基，可选取代的低碳烯基，可选取代的芳基，可选取代的杂环基或可选取代的氨基；R4为氢，可选取代的低碳基，可选取代的芳基或可选取代的杂环基；R5为氢，可选取代的低碳基，可选取代的芳基或可选取代的杂环基；R10为羟基或受保护的羟基，并且其药学上可接受的盐。该化合物可用作MMP或TNFα介导疾病的预防和治疗药物。
• Piperazine compounds as inhibitors of MMP or TNF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：US20030060473A1

  公开（公告）日：2003-03-27

  A compound of formula (I) wherein A is a sulfonyl or a carbonyl; R 1 is an optionally substituted aryl, an optionally substituted heterocyclic group, an optionally substituted lower alkyl or an optionally substituted lower alkenyl; R 2 is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; R 3 is an optionally substituted lower alkyl, an optionally substituted lower alkoxy, an optionally substituted aryloxy, an optionally substituted lower alkenyl, an optionally substituted aryl, an optionally substituted heterocyclic group or an optionally substituted amino; R 4 is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; R 5 is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; and R 10 is a hydroxy or a protected hydroxy, and a pharmaceutically acceptable salt thereof. The compound of the present invention is useful as a medicament for prophylactic and therapeutic treatment of MMP-or TNF&agr;-medicated diseases.

  化合物公式（I）其中A是磺酰基或羰基；R1是可选择取代的芳基、可选择取代的杂环基团、可选择取代的低级烷基或可选择取代的低级烯基；R2是氢、可选择取代的低级烷基、可选择取代的芳基或可选择取代的杂环基团；R3是可选择取代的低级烷基、可选择取代的低级烷氧基、可选择取代的芳氧基、可选择取代的低级烯基、可选择取代的芳基、可选择取代的杂环基团或可选择取代的氨基；R4是氢、可选择取代的低级烷基、可选择取代的芳基或可选择取代的杂环基团；R5是氢、可选择取代的低级烷基、可选择取代的芳基或可选择取代的杂环基团；R10是羟基或保护羟基，以及其药学上可接受的盐。本发明的化合物可用作预防和治疗MMP或TNF-α介导疾病的药物。
• Cyclopropane compounds and pharmaceutical use thereof
  申请人：Inaba Takashi

  公开号：US20060199826A1

  公开（公告）日：2006-09-07

  The present invention provides a compound having aggrecanase inhibitory activity and MMP-13 inhibitory activity, and useful as a therapeutic agent for osteoarthritis, rheumatoid arthritis and the like, more specifically, a cyclopropane compound of formula (1): wherein R 1 is —(CH 2 ) m —X—(CH 2 ) n -A 1 etc., wherein m and n are the same or different and each is 0 to 6, X 1 is a single bond, etc. and A 1 is a substituted C 3-14 hydrocarbon ring group, etc.; R 2 and R 3 are the same or different and each is a hydrogen atom, —(CH 2 ) p —X 1 -(CH 2 ) q -A 2 , etc., wherein p and q are the same or different and each is 0 to 6, X 1 is a single bond, etc. and A 2 is an optionally substituted C 3-14 hydrocarbon ring group, etc.; R 4 is —CO 2 R 9 , etc., wherein R 9 is a hydrogen atom, etc.; and R 20 and R 21 are the same or different and each is a hydrogen atom, —(CH 2 ) m12 —X 12 —(CH 2 ) m12 —R 30 , etc., wherein m12 and m12 are the same or different and each is 0 to 6, X 12 is a single bond, etc. and R 30 is a hydrogen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有抗软骨素酶活性和MMP-13抑制活性的化合物，可用作治疗骨关节炎、类风湿性关节炎等疾病的治疗剂，更具体地，是一种环丙烷化合物，其化学式为（1）：其中，R1为—（CH2）m—X—（CH2）n-A1等，其中m和n相同或不同，且每个为0至6，X1为单键等，A1为取代的C3-14碳氢环基等；R2和R3相同或不同，且每个为氢原子，—（CH2）p—X1-（CH2）q-A2等，其中p和q相同或不同，且每个为0至6，X1为单键等，A2为可选取代的C3-14碳氢环基等；R4为—CO2R9等，其中R9为氢原子等；且R20和R21相同或不同，且每个为氢原子，—（CH2）m12—X12—（CH2）m12—R30等，其中m12和m12相同或不同，且每个为0至6，X12为单键等，R30为氢原子等；或其前药或其药学上可接受的盐。
• N-substituted-n-sulfonylaminocyclopropane compounds and pharmaceutical use thereof
  申请人：Fryer M. Andrew

  公开号：US20050222146A1

  公开（公告）日：2005-10-06

  The present invention provides a compound having aggrecanase inhibitory activity and MMP-13 inhibitory activity, and useful as a therapeutic agent for osteoarthritis, rheumatoid arthritis and the like, more specifically, a N-substituted-N-sulfonylaminocyclopropane compound of formula (1): wherein R 1 is —W-A 1 —W 1 -A 2 , W is —(CH 2 ) m —X—(CH 2 ) n —, wherein W 1 is —(CH 2 ) m1 —X 1 —(CH 2 ) n1 —, m, m1, n and n1 are the same or different and each is 0 to 6, X and X 1 are the same or different and each is a single bond, etc., A 1 is an optionally substituted C 3-14 hydrocarbon ring group, etc. and A 2 is a substituted C 3-14 hydrocarbon ring group etc.; R 2 is —(CH 2 ) r —CO—R 8 , etc., wherein r is 0 to 6 and R 8 is a C 1-6 alkoxy group, etc.; R 3 and R 4 are the same or different and each is a hydrogen atom, a C 1-6 alkyl group, etc.; and R 5 is —CO 2 R 21 etc.; R 30 and R 31 are the same or different and each is a hydrogen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有抑制聚集素酶活性和MMP-13抑制活性的化合物，可用作治疗骨关节炎、类风湿性关节炎等疾病的治疗剂，更具体地说，是式（1）的N-取代-N-磺酰基环丙烷化合物： 其中，R1为—W-A1—W1-A2，W为—（CH2）m—X—（CH2）n—，其中W1为—（CH2）m1—X1—（CH2）n1—，m、m1、n和n1相同或不同，每个为0到6，X和X1相同或不同，每个为单键等；A1为可选取代的C3-14碳氢环基等，A2为取代的C3-14碳氢环基等；R2为—（CH2）r—CO—R8等，其中r为0到6，R8为C1-6烷氧基等；R3和R4相同或不同，每个为氢原子、C1-6烷基等；R5为—CO2R21等；R30和R31相同或不同，每个为氢原子等；或其前药或药学上可接受的盐。