4-(2H-[1,2,3]三唑-2-基)苯磺酰氯 | 517919-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(2H-[1,2,3]三唑-2-基)苯磺酰氯
• 英文名称: 4-(2H-[1,2,3]triazol-2-yl)benzenesulfonyl chloride
• 英文别名: 4-(2H-triazol-2-yl)benzenesulfonyl chloride；4-[1,2,3]triazol-2-yl-benzenesulfonyl chloride；4-[1,2,3]Triazol-2-yl-benzolsulfonylchlorid；4-(2H-1,2,3-triazol-2-yl)benzene-1-sulfonyl chloride；4-(triazol-2-yl)benzenesulfonyl chloride
• CAS: 517919-17-4
• 化学式: C₈H₆ClN₃O₂S
• mdl: MFCD19200315
• 分子量: 243.674
• InChiKey: NJJPEXICSUBIBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  402.2±47.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 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：
  73.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2H-[1,2,3]三唑-2-基)苯磺酰氯 在 氨 、 水 作用下， 生成 4-[1,2,3]triazol-2-yl-benzenesulfonic acid amide
  参考文献：
  名称：

  2-苯基-2,1,3-三唑及其衍生物。

  摘要：

  DOI：

  10.1021/jo01164a005
• 作为产物：
  描述：

  2-苯基-2H- 1,2,3-三氮唑 在 氯磺酸 作用下， 以70.4%的产率得到4-(2H-[1,2,3]三唑-2-基)苯磺酰氯
  参考文献：
  名称：

  Tetrahydroisoquinoline-3-carboxylate based matrix-metalloproteinase inhibitors: design, synthesis and structure–activity relationship

  摘要：

  The design, synthesis and structure-activity relationship (SAR) of a series of nonpeptidic 2-arylsulfonyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxylates and-hydroxamates as inhibitors of the matrix metalloproteinase human neutrophil collagenase (MMP-8) is described here. Based on available X-ray structures of MMP-8/inhibitor complexes, our structure-based design strategy was directed to complement major protein-ligand interaction regions mainly in the S1' hydrophobic specificity pocket close to the catalytic zinc ion. Here, the rigid 1,2,3,4-tetrahydroisoquinoline scaffold (Tic) provides ideal geometry to combine hydroxamates and carboxylates as typical zinc complexing functionalities, with a broad variety of S1' directed mono- and biaryl substituents consisting of aromatic rings perfectly accommodated within this more hydrophobic region of the MMP-8 inhibitor binding site. The effect of different S1' directed substituents, zinc-complexing groups, chirality and variations of the tetrahydroisoquinoline ring-system is investigated by systematic studies. X-ray structure analyses in combination with 3D-QSAR studies provided an additional understanding of key determinants for MMP-8 affinity in this series. The hypothetical binding mode for a typical molecule as basis for our inhibitor design was found in good agreement with a 1.7 Angstrom X-ray structure of this candidate in complex with the catalytic domain of human MMP-8. After analysis of all systematic variations, 3D-QSAR and X-ray structure analysis, novel S1' directed substituents were designed and synthesized and biologically evaluated. This finally results in inhibitors, which do not only show high biological affinity for MMP-8, but also exhibit good oral bioavailability in several animal species. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00215-8

文献信息

• [EN] HIV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTÉASE DU VIH
  申请人：MERCK CANADA INC

  公开号：WO2013059928A1

  公开（公告）日：2013-05-02

  Compounds of Formula I are disclosed: wherein A, R1, R2, R3, R4A, R4B, R5, R6 and R7 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式I的化合物已被披露：其中A、R1、R2、R3、R4A、R4B、R5、R6和R7在此定义。公式I包括HIV蛋白酶抑制剂的化合物。公式I所包括的化合物及其药学上可接受的盐对于预防或治疗HIV感染以及预防、治疗或延缓艾滋病的发作是有用的。这些化合物及其盐可作为药物组合物的成分，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用。
• HIV PROTEASE INHIBITORS
  申请人：MERCK CANADA INC.

  公开号：US20140303171A1

  公开（公告）日：2014-10-09

  Compounds of Formula I are disclosed: wherein A, R 1 , R 2 , R 3 , R 4A , R 4B , R 5 , R 6 and R 7 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公开了I式化合物：其中A，R1，R2，R3，R4A，R4B，R5，R6和R7的定义如下。公式I所包含的化合物包括HIV蛋白酶抑制剂。公式I所涵盖的化合物及其药学上可接受的盐对于预防或治疗HIV感染以及预防，治疗或延迟AIDS的发作非常有用。这些化合物及其盐可以作为药物组成部分，可以与其他抗病毒药物，免疫调节剂，抗生素或疫苗组合使用。
• Thiophen and thiazol sulfonamid derivatives as HIV protease inhibitors for the treatment of AIDS
  申请人：Merck Canada Inc.

  公开号：EP2771332B1

  公开（公告）日：2016-06-29
• US9133157B2
  申请人：——

  公开号：US9133157B2

  公开（公告）日：2015-09-15
• Tetrahydroisoquinoline-3-carboxylate based matrix-metalloproteinase inhibitors: design, synthesis and structure–activity relationship
  作者：Hans Matter、Manfred Schudok、Wilfried Schwab、Werner Thorwart、Denis Barbier、Günter Billen、Burkhard Haase、Bernhard Neises、Klaus-Ulrich Weithmann、Theo Wollmann

  DOI：10.1016/s0968-0896(02)00215-8

  日期：2002.11

  The design, synthesis and structure-activity relationship (SAR) of a series of nonpeptidic 2-arylsulfonyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxylates and-hydroxamates as inhibitors of the matrix metalloproteinase human neutrophil collagenase (MMP-8) is described here. Based on available X-ray structures of MMP-8/inhibitor complexes, our structure-based design strategy was directed to complement major protein-ligand interaction regions mainly in the S1' hydrophobic specificity pocket close to the catalytic zinc ion. Here, the rigid 1,2,3,4-tetrahydroisoquinoline scaffold (Tic) provides ideal geometry to combine hydroxamates and carboxylates as typical zinc complexing functionalities, with a broad variety of S1' directed mono- and biaryl substituents consisting of aromatic rings perfectly accommodated within this more hydrophobic region of the MMP-8 inhibitor binding site. The effect of different S1' directed substituents, zinc-complexing groups, chirality and variations of the tetrahydroisoquinoline ring-system is investigated by systematic studies. X-ray structure analyses in combination with 3D-QSAR studies provided an additional understanding of key determinants for MMP-8 affinity in this series. The hypothetical binding mode for a typical molecule as basis for our inhibitor design was found in good agreement with a 1.7 Angstrom X-ray structure of this candidate in complex with the catalytic domain of human MMP-8. After analysis of all systematic variations, 3D-QSAR and X-ray structure analysis, novel S1' directed substituents were designed and synthesized and biologically evaluated. This finally results in inhibitors, which do not only show high biological affinity for MMP-8, but also exhibit good oral bioavailability in several animal species. (C) 2002 Elsevier Science Ltd. All rights reserved.