5-bromo-4-chlorothiophene-2-sulfonamide | 77893-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-bromo-4-chlorothiophene-2-sulfonamide
• CAS: 77893-75-5
• 化学式: C₄H₃BrClNO₂S₂
• mdl: MFCD00177162
• 分子量: 276.562
• InChiKey: PRKDIXNPZQMOAL-UHFFFAOYSA-N

物化性质

• 熔点：
  159.5-161.5 °C
• 沸点：
  428.7±55.0 °C(Predicted)
• 密度：
  2.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-4-chlorothiophene-2-sulfonamide 在 锌 乙酸乙酯 、 Sodium sulfate-III 、 crude product 、 silica gel 、 二氯甲烷 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以to afford the title compound (0.88 g, 52%)的产率得到4-chlorothiophene-2-sulfonamide
  参考文献：
  名称：

  Thiophene-amd thiazolesulfonamides as antineoplastic agents

  摘要：

  本发明提供了式子所示的抗肿瘤化合物，以及抗肿瘤方法。

  公开号：

  US07084170B2
• 作为产物：
  描述：

  5-bromo-4-chlorothiophene-2-sulfonyl chloride 在 ammonium hydroxide 作用下， 以 丙酮 为溶剂， 生成 5-bromo-4-chlorothiophene-2-sulfonamide
  参考文献：
  名称：

  Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 3. 5-(Arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides

  摘要：

  A series of 5-(arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides is described and anticonvulsant activities are listed for the compounds. In most cases, the sulfones had the highest activity and the sulfides the least. Sulfones with 3- or 4-halo substituents generally had the highest activity, and one analogue, 5-[(4-fluorophenyl)sulfonyl]thiophene-2-sulfonamide (51, UK-17022), had an anticonvulsant ED50 fo 2 mg/kg when administered orally to mice. Compound 51 selectively increased cerebral blood flow in animals without an unacceptable level of diuresis.

  DOI：

  10.1021/jm00140a009

文献信息

• [EN] 2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE<br/>[FR] COMPOSÉS DE 2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDÈNE)ACÉTAMIDE ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：OXFORD DRUG DESIGN LTD

  公开号：WO2021123237A1

  公开（公告）日：2021-06-24

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些2-氨基-N-(氨基氧代芳基-λ6-砜基)乙酰胺化合物（以下简称为ANASIA化合物），该化合物在一些情况下抑制（例如，选择性抑制）细菌氨酰-tRNA合成酶（aaRS）（例如，细菌亮氨酰-tRNA合成酶，LeuRS）。本发明还涉及包含这种化合物的药物组合物，以及在体内外使用这种化合物和组合物来抑制（例如，选择性抑制）细菌氨酰-tRNA合成酶；治疗通过抑制（例如，选择性抑制）细菌氨酰-tRNA合成酶而得到改善的疾病；治疗细菌感染等。
• Thiophene-amd thiazolesulfonamides as antineoplastic agents
  申请人：Eli Lilly and Company

  公开号：US07084170B2

  公开（公告）日：2006-08-01

  The present invention provides antineoplastic compounds of the formula: and antineoplastic methods.

  本发明提供了式子所示的抗肿瘤化合物，以及抗肿瘤方法。
• Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 3. 5-(Arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides
  作者：Ian T. Barnish、Peter E. Cross、Roger P. Dickinson、Michael J. Parry、Michael J. Randall

  DOI：10.1021/jm00140a009

  日期：1981.8

  A series of 5-(arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides is described and anticonvulsant activities are listed for the compounds. In most cases, the sulfones had the highest activity and the sulfides the least. Sulfones with 3- or 4-halo substituents generally had the highest activity, and one analogue, 5-[(4-fluorophenyl)sulfonyl]thiophene-2-sulfonamide (51, UK-17022), had an anticonvulsant ED50 fo 2 mg/kg when administered orally to mice. Compound 51 selectively increased cerebral blood flow in animals without an unacceptable level of diuresis.
• BARNISH, I. T.;CROSS, P. E.;DICKINSON, R. P.;PARRY, M. J.;RANDALL, M. J., J. MED. CHEM., 1981, 24, N 8, 959-964
  作者：BARNISH, I. T.、CROSS, P. E.、DICKINSON, R. P.、PARRY, M. J.、RANDALL, M. J.

  DOI：——

  日期：——
• Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives
  作者：Mary M. Mader、Chuan Shih、Eileen Considine、Alfonso De Dios、Cora Sue Grossman、Philip A. Hipskind、Ho-Shen Lin、Karen L. Lobb、Beatriz Lopez、José E. Lopez、Luisa M. Martin Cabrejas、Michael E. Richett、Wesley T. White、Yiu-Yin Cheung、Zhongping Huang、John E. Reilly、Sean R. Dinn

  DOI：10.1016/j.bmcl.2004.11.041

  日期：2005.2

  The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay. (C) 2004 Elsevier Ltd. All rights reserved.