4-bromo-3-(morpholinosulfonyl)benzoic acid | 300383-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-3-(morpholinosulfonyl)benzoic acid
• 英文别名: 4-Bromo-3-(morpholine-4-sulfonyl)-benzoic acid；4-bromo-3-morpholin-4-ylsulfonylbenzoic acid
• CAS: 300383-13-5
• 化学式: C₁₁H₁₂BrNO₅S
• mdl: MFCD00625739
• 分子量: 350.19
• InChiKey: RMFTWSQXRNWNMA-UHFFFAOYSA-N

物化性质

• 沸点：
  536.8±60.0 °C(Predicted)
• 密度：
  1.712±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-bromo-3-(morpholinosulfonyl)benzoic acid 在 四(三苯基膦)钯 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists

  摘要：

  Screening efforts identified (bis)sulfonic acid. (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated CAMP accumulation with IC50 values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC50 values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC50 value of 0.9 muM in the FSHR-cAMP assay was essentially inactive at 30muM in the TSHR-cAMP assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00324-8
• 作为产物：
  描述：

  4-溴苯甲酸 在 氯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 4-bromo-3-(morpholinosulfonyl)benzoic acid
  参考文献：
  名称：

  Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists

  摘要：

  Screening efforts identified (bis)sulfonic acid. (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated CAMP accumulation with IC50 values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC50 values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC50 value of 0.9 muM in the FSHR-cAMP assay was essentially inactive at 30muM in the TSHR-cAMP assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00324-8

文献信息

• Sulfamoyl benzamides as novel CB2 cannabinoid receptor ligands
  作者：Karin Worm、Q. Jean Zhou、Christopher T. Saeui、Rosalyn C. Green、Joel A. Cassel、Gabriel J. Stabley、Robert N. DeHaven、Nathalie Conway-James、Christopher J. LaBuda、Michael Koblish、Patrick J. Little、Roland E. Dolle

  DOI：10.1016/j.bmcl.2008.04.006

  日期：2008.5

  Sulfamoyl benzamides were identified as a novel series of cannabinoid receptor ligands. Starting from a screening hit 8 that had modest affinity for the cannabinoid CB(2) receptor, a parallel synthesis approach and initial SAR are described, leading to compound 27 with 120-fold functional selectivity for the CB(2) receptor. This compound produced robust antiallodynic activity in rodent models of postoperative

  氨磺酰基苯甲酰胺被确定为一系列新的大麻素受体配体。从对大麻素CB（2）受体具有适度亲和力的筛选命中8开始，描述了一种平行合成方法和初始SAR，从而导致化合物27对CB（2）受体的功能选择性为120倍。该化合物在术后疼痛和神经性疼痛的啮齿动物模型中产生了强大的抗痛觉过敏活性，而没有传统的大麻素副作用。
• Sulfamoyl Benzamides and Methods of Their Use
  申请人：Dolle E. Roland

  公开号：US20080058302A1

  公开（公告）日：2008-03-06

  Novel sulfamoyl benzamide compounds, pharmaceutical compositions containing the sulfamoyl benzamide compounds, and methods of their pharmaceutical use are disclosed. In certain embodiments, the sulfamoyl benzamide compounds are agonists and/or ligands of cannabinoid receptors and may be useful, inter alia, for treating and/or preventing pain, gastrointestinal disorders, inflammation, auto-immune diseases, ischemic conditions, immune-related disorders, hypertension, neurological disorders, and neurodegenerative diseases, for providing cardioprotection against ischemic and reperfusion effects, for inducing apoptosis in malignant cells, for inhibiting mechanical hyperalgesia associated with nerve injury, and as an appetite stimulant.

  本发明涉及新型磺酰胺苯甲酰胺化合物、含有该磺酰胺苯甲酰胺化合物的制药组合物以及它们的制药用途的方法。在某些实施例中，该磺酰胺苯甲酰胺化合物是大麻素受体的激动剂和/或配体，可用于治疗和/或预防疼痛、胃肠障碍、炎症、自身免疫性疾病、缺血性疾病、免疫相关疾病、高血压、神经系统疾病和神经退行性疾病，提供对缺血和再灌注效应的心脏保护作用，诱导恶性细胞凋亡，抑制与神经损伤相关的机械性高痛敏，并作为食欲刺激剂。
• Sulfamoyl benzamides and methods of their use
  申请人：Adolor Corporation

  公开号：US07544676B2

  公开（公告）日：2009-06-09

  Novel sulfamoyl benzamide compounds, pharmaceutical compositions containing the sulfamoyl benzamide compounds, and methods of their pharmaceutical use are disclosed. In certain embodiments, the sulfamoyl benzamide compounds are agonists and/or ligands of cannabinoid receptors and may be useful, inter alia, for treating and/or preventing pain, gastrointestinal disorders, inflammation, auto-immune diseases, ischemic conditions, immune-related disorders, hypertension, neurological disorders, and neurodegenerative diseases, for providing cardioprotection against ischemic and reperfusion effects, for inducing apoptosis in malignant cells, for inhibiting mechanical hyperalgesia associated with nerve injury, and as an appetite stimulant.

  本发明揭示了新型磺酰胺苯甲酰胺化合物、含有该磺酰胺苯甲酰胺化合物的制药组合物以及它们的制药应用方法。在某些实施例中，磺酰胺苯甲酰胺化合物是大麻素受体的激动剂和/或配体，可能有助于治疗和/或预防疼痛、胃肠道疾病、炎症、自身免疫疾病、缺血性疾病、免疫相关疾病、高血压、神经系统疾病和神经退行性疾病，提供对缺血和再灌注效应的心脏保护，诱导恶性细胞凋亡，抑制与神经损伤相关的机械性高痛敏，以及作为食欲刺激剂。
• WO2007/58960
  申请人：——

  公开号：——

  公开（公告）日：——
• US7544676B2
  申请人：——

  公开号：US7544676B2

  公开（公告）日：2009-06-09