2-(4-Bromobutyl)-1,1-dioxido-5-nitro-1,2-benzothiazol-3(2H)-one | 173842-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4-Bromobutyl)-1,1-dioxido-5-nitro-1,2-benzothiazol-3(2H)-one
• 英文别名: 2-(4-bromobutyl)-5-nitro-1,1-dioxido-1,2-benzothiazol-3(2H)-one；2-(4-bromobutyl)-1,1-dioxido-5-nitro-1,2-benzisothiazol-3(2H)-one；2-(4-bromobutyl)-5-nitro-1,1-dioxo-1,2-benzothiazol-3-one
• CAS: 173842-20-1
• 化学式: C₁₁H₁₁BrN₂O₅S
• 分子量: 363.189
• InChiKey: HVTAASYUPOJRNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-哌啶)1,3-苯并恶唑-2-(3H)酮 、 2-(4-Bromobutyl)-1,1-dioxido-5-nitro-1,2-benzothiazol-3(2H)-one 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,1-Dioxido-2-(4-(4-(2-oxo-3-benzoxazolinyl)-piperidin-1-yl)-butyl)-5-nitro-1,2-benzisothiazol-3(2H)-one
  参考文献：
  名称：

  Design and synthesis of N-alkylated saccharins as selective α-1a adrenergic receptor antagonists

  摘要：

  Benign prostatic hyperplasia can be managed pharmacologically with alpha-1 adrenergic receptor antagonists. Agents that demonstrate selectivity for the alpha-1a receptor subtype may offer advantages in clinical applications with respect to hypotensive side effects. The N-alkylated saccharins reported here represent a new class of subtype selective alpha-1a adrenergic receptor antagonists which demonstrate potent effects on prostate function in vivo and are devoid of blood pressure side effects. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00446-6
• 作为产物：
  描述：

  1,4-二溴丁烷 、 5-nitro-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one; sodium salt 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-Bromobutyl)-1,1-dioxido-5-nitro-1,2-benzothiazol-3(2H)-one
  参考文献：
  名称：

  Design and synthesis of N-alkylated saccharins as selective α-1a adrenergic receptor antagonists

  摘要：

  Benign prostatic hyperplasia can be managed pharmacologically with alpha-1 adrenergic receptor antagonists. Agents that demonstrate selectivity for the alpha-1a receptor subtype may offer advantages in clinical applications with respect to hypotensive side effects. The N-alkylated saccharins reported here represent a new class of subtype selective alpha-1a adrenergic receptor antagonists which demonstrate potent effects on prostate function in vivo and are devoid of blood pressure side effects. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00446-6

文献信息

• Alpha IC adrenergic receptor antagonists
  申请人：Merck & Co., Inc.

  公开号：US05760054A1

  公开（公告）日：1998-06-02

  This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as selective alpha-1C adrenergic receptor antagonists. One application of these compounds is in the treatment of benign prostatic hypertrophy. These compounds are selective in their ability to relax smooth muscle tissue enriched in the alpha1C receptor subtype without at the same time inducing orthostatic hypotension. One such tissue is found surrounding the urethral lining. Therefore, one utility of the instant compounds is to provide acute relief to males suffering from benign prostatic hyperplasia, by permitting less hindered urine flow. Another utility of the instant compounds is provided by combination with a human 5-alpha reductase inhibitory compound, such that both acute and chronic relief from the effects of benign prostatic hyperplasia are achieved.

  这项发明涉及某些新型化合物及其衍生物，它们的合成以及它们作为选择性α-1C肾上腺素受体拮抗剂的用途。这些化合物的一个应用是治疗良性前列腺肥大。这些化合物在其能够放松富含α1C受体亚型的平滑肌组织方面具有选择性，同时不会引起直立性低血压。这样的组织之一是围绕尿道内衬的组织。因此，这些化合物的一个用途是通过减少阻碍尿液流动来为患有良性前列腺增生的男性提供急性缓解。这些化合物的另一个用途是与人类5α-还原酶抑制剂化合物结合，从而实现对良性前列腺增生影响的急性和慢性缓解。
• ALPHA1C ADRENERGIC RECEPTOR ANTAGONISTS
  申请人：Merck & Co., Inc.

  公开号：EP0755392A1

  公开（公告）日：1997-01-29
• EP0755392A4
  申请人：——

  公开号：EP0755392A4

  公开（公告）日：1997-05-02
• US5760054A
  申请人：——

  公开号：US5760054A

  公开（公告）日：1998-06-02
• [EN] ALPHA1C ADRENERGIC RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR ADRENERGIQUE ALPHA1C
  申请人：MERCK & CO., INC.

  公开号：WO1995028397A1

  公开（公告）日：1995-10-26

  (EN) This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as selective alpha1C adrenergic receptor antagonists. One application of these compounds is in the treatment of benign prostatic hypertrophy. These compounds are selective in their ability to relax smooth muscle tissue enriched in the alpha1C receptor subtype without at the same time inducing orthostatic hypotension. One such tissue is found surrounding the urethral lining. Therefore, one utility of the instant compounds is to provide acute relief to males suffering from benign prostatic hyperplasia, by permitting less hindered urine flow. Another utility of the instant compounds is provided by combination with a human 5-alpha reductase inhibitory compound, such that both acute and chronic relief from the effects of benign prostatic hyperplasia are achieved.(FR) L'invention porte sur certains composés nouveaux, leurs dérivés, leur synthèse et leur utilisation en tant qu'antagonistes sélectifs du récepteur adrénergique alpha1C. L'une de leurs applications réside dans le traitement de l'hypertrophie bénigne de la prostate. Ces composés présentent une capacité sélective de relaxation des tissus de muscles lisses enrichis en sous-catégorie du récepteur alpha1-C sans pour autant provoquer d'hypotension orthostatique. L'un de ces tissus entoure l'endothélium de l'urètre. L'un des intérêts de ces composés à action instantanée est donc d'apporter un soulagement rapide aux patients souffrant d'hypertrophie bénigne de la prostate en réduisant les obstacles au flux urinaire, un autre étant que, combinés avec un composé inhibiteur de la 5-alpha réductase humaine, ils peuvent soulager les effets aigus et chroniques de ladite hypertrophie.