4-[4,5-二氢-5-(1H-吲哚)-3-(三氟甲基)-1h-吡唑]-苯磺酰胺 | 313236-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[4,5-二氢-5-(1H-吲哚)-3-(三氟甲基)-1h-吡唑]-苯磺酰胺
• 英文名称: 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-(3-indolyl)-2-pyrazoline
• 英文别名: 4-[3-(1H-indol-3-yl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide
• CAS: 313236-73-6；787623-45-4；787623-46-5
• 化学式: C₁₈H₁₅F₃N₄O₂S
• 分子量: 408.404
• InChiKey: VUSRFTDIRYHHTA-UHFFFAOYSA-N

物化性质

• 沸点：
  587.2±60.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[4,5-二氢-5-(1H-吲哚)-3-(三氟甲基)-1h-吡唑]-苯磺酰胺 在 溴 作用下， 以 水 为溶剂， 反应 8.0h， 生成 4-[5-(3-indolyl)-3(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors

  摘要：

  A series of 20 novel 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines were designed, synthesized, and screened in vitro for anti-inflammatory activity. These compounds were designed for evaluation as dual inhibitors of cyclooxygenases (COX-1 and COX-2) and lipoxygenases (LOX-5, LOX-12, and LOX-15) that are responsible for inflammation and pain. All pyrazoline molecules prepared are optically active and compounds that are more potent in COX-2 inhibitory activity (5a and 5f) were resolved by chiral column and each enantiomer was tested for cyclooxygenase inhibitory activity. Molecular modeling and comparison of molecular models of 5a enantiomers with that of celecoxib model shows that 5a (enantiomer-1) and 5a (enantiomer-2) have more hydrogen bonding interactions in the catalytic domain of COX-2 enzyme than celecoxib. Compounds 5a, 5e, and 5f showed moderate to good LOX-5 and LOX-15 inhibitory activity and this is comparable to that of celecoxib and more potent than rofecoxib. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.047
• 作为产物：
  描述：

  4-磺酰胺基苯肼盐酸盐 、 反-1,1,1-三氟-4-(3-吲哚基)-3-丁烯-2-酮 以The title compound was obtained in 82% yield, m.p. 178-180° C.的产率得到4-[4,5-二氢-5-(1H-吲哚)-3-(三氟甲基)-1h-吡唑]-苯磺酰胺
  参考文献：
  名称：

  Pyrazoline derivatives useful for the treatment of cancer

  摘要：

  化合物的公式（I），其中： X被选自三卤甲基，C1-C6烷基和公式（II）中的一组，其中： R3和R4分别被选自氢，卤素，羟基，硝基，C1-C6烷基，C1-C6烷氧基，羧基，C1-C6三卤代烷基和氰基的一组； Z被选自取代和未取代芳基；或其药学上可接受的盐。这些化合物是环氧合酶-2活性的抑制剂。它们可用于治疗环氧合酶介导的疾病，包括例如炎症，肿瘤性疾病和血管生成介导的疾病。

  公开号：

  US20070066651A1

文献信息

• 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines and inhibitors of cyclooxygenase-2
  申请人：Temple University-of the Commonwealth of Higher Education

  公开号：US06376519B1

  公开（公告）日：2002-04-23

  Compounds of the formula wherein: X is selected from the group consisting of trihalomethyl, C1-C6 alkyl, and a group of formula II: wherein: R3 and R4 are independently selected from the group consisting of hydrogen; halogen; hydroxyl; nitro; C1-C6 alkyl; C1-C6 alkoxy; carboxy; C1-C6 trihaloalkyl; and cyano; Z is selected from the group consisting of substituted and unsubstituted aryl; or a pharmaceutically acceptable salt thereof. The compounds are inhibitors of cyclooxygenase-2 activity. They are useful for treating cyclooxygenase-mediated disorders, including, for example, inflamation, neoplastic disorders and angiogenesis-mediated disorders.

  该式化合物中，X选择自三卤甲基、C1-C6烷基和式II的基团，其中：R3和R4独立选择自氢、卤素、羟基、硝基、C1-C6烷基、C1-C6烷氧基、羧基、C1-C6三卤基烷基和氰基；Z选择自取代和未取代芳基；或其药学上可接受的盐。这些化合物是环氧合酶-2活性的抑制剂。它们可用于治疗环氧合酶介导的疾病，包括炎症、肿瘤性疾病和血管生成介导的疾病。
• USRE039681E1
  申请人：——

  公开号：——

  公开（公告）日：——
• 1-(4-SULFAMYLARYL)-3-SUBSTITUTED-5-ARYL-2-PYRAZOLINES AS INHIBITORS OF CYCLOOXYGENASE-2
  申请人：Temple University of the CommonwealthSystem of Higher Education

  公开号：EP1191931A1

  公开（公告）日：2002-04-03
• EP1191931A4
  申请人：——

  公开号：EP1191931A4

  公开（公告）日：2002-11-27
• 1-(4-SULFAMYLPHENYL)-3-TRIFLUOROMETHYL-5-ARYL-2-PYRAZOLINES AS INHIBITORS OF CYCLOOXYGENASE-2
  申请人：Temple University of the Commonwealth System of Higher Education

  公开号：EP1191931B1

  公开（公告）日：2007-05-09