2,3-Dichloro-4-(2-propan-2-ylphenyl)sulfanylbenzaldehyde | 387873-65-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-Dichloro-4-(2-propan-2-ylphenyl)sulfanylbenzaldehyde
• CAS: 387873-65-6
• 化学式: C₁₆H₁₄Cl₂OS
• 分子量: 325.259
• InChiKey: ABVJZLLWUVTBHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Dichloro-4-(2-propan-2-ylphenyl)sulfanylbenzaldehyde 在 sodium hydroxide 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists

  摘要：

  Diarylsulfide cyclopropylamides were synthesized and evaluated as LFA-1/ICAM-1 interaction antagonists. A substituent pattern was identified which maximized potency and minimized protein binding as exemplified by antagonist 30 (IC50 = 5 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00105-6
• 作为产物：
  描述：

  2,3-二氯-4-羟基苯甲醛 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 1.42h， 生成 2,3-Dichloro-4-(2-propan-2-ylphenyl)sulfanylbenzaldehyde
  参考文献：
  名称：

  Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists

  摘要：

  Diarylsulfide cyclopropylamides were synthesized and evaluated as LFA-1/ICAM-1 interaction antagonists. A substituent pattern was identified which maximized potency and minimized protein binding as exemplified by antagonist 30 (IC50 = 5 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00105-6

文献信息

• Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents
  申请人：——

  公开号：US20020156314A1

  公开（公告）日：2002-10-24

  The present invention relates to novel cyclopropane-containing diaryl sulfide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及可用于治疗炎症和免疫疾病的新型含环丙烷二芳基硫醚化合物，涉及包含这些化合物的药物组合物，还涉及抑制哺乳动物炎症或抑制免疫反应的方法。
• Discovery of Novel <i>p</i>-Arylthio Cinnamides as Antagonists of Leukocyte Function-Associated Antigen-1/Intercellular Adhesion Molecule-1 Interaction. 4. Structure−Activity Relationship of Substituents on the Benzene Ring of the Cinnamide
  作者：Martin Winn、Edward B. Reilly、Gang Liu、Jeffrey R. Huth、Hwan-Soo Jae、Jennifer Freeman、Zhonghua Pei、Zhili Xin、John Lynch、Jeff Kester、Thomas W. von Geldern、Sandra Leitza、Peter DeVries、Robert Dickinson、Donna Mussatto、Gregory F. Okasinski

  DOI：10.1021/jm0103108

  日期：2001.12.1

  We have shown that p-arylthio cinnamides can inhibit the interaction of LFA-1 and ICAM-1, which is involved in cell adhesion and the inflammatory process. We now show that 2,3-disubstitution on the aryl portion of the cinnamide results in enhanced activity over mono substitution on the ring. The best 2,3-substituents were chlorine and trifluoromethyl groups. Compounds 39 and 40 which contain two CF3 groups have IC50 values of 0.5 and 0.1 nM, respectively, in inhibiting JY8 cells expressing LFA-1 on their surface, from adhering to ICAM-1. The structure-activity relationship (SAR) was examined using an NMR based model of the LFA-1 I domain/compound 31 complex. One of our compounds (38) was able to reduce cell migration in two different in vivo experiments.
• ARYL PHENYCYCLOPROPYL SULFIDE DERIVATIVES AND THEIR USE AS CELL ADHESION-INHIBITING ANTI-INFLAMMATORY AND IMMUNE-SUPPRESSIVE AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1294685A1

  公开（公告）日：2003-03-26
• US6521619B2
  申请人：——

  公开号：US6521619B2

  公开（公告）日：2003-02-18
• [EN] ARYL PHENYCYCLOPROPYL SULFIDE DERIVATIVES AND THEIR USE AS CELL ADHESION-INHIBITING ANTI-INFLAMMATORY AND IMMUNE-SUPPRESSIVE AGENTS<br/>[FR] DERIVES DE SULFURE D'ARYLE PHENYCYCLOPROPYLE ET LEUR UTILISATION EN TANT QUE COMPOSES ANTI-INFLAMMATOIRES INHIBANT L'ADHESION CELLULAIRE ET AGENTS IMMUNOSUPPRESSEURS
  申请人：ABBOTT LAB

  公开号：WO2002002522A1

  公开（公告）日：2002-01-10

  The present invention relates to novel cyclopropane-containing diaryl sulfide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.