ethyl 3-((4-bromophenyl)sulfonamido)benzoate | 349614-31-9

• 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: ethyl 3-((4-bromophenyl)sulfonamido)benzoate
• 英文别名: Ethyl 3-[(4-bromophenyl)sulfonylamino]benzoate
• CAS: 349614-31-9
• 化学式: C₁₅H₁₄BrNO₄S
• 分子量: 384.25
• InChiKey: OCBDYHJKMYHJNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-((4-bromophenyl)sulfonamido)benzoate 在 四(三苯基膦)钯 、 sodium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 3-(2',4'-dichlorobiphenyl-4-ylsulfonamido)benzoic acid
  参考文献：
  名称：

  Development of triarylsulfonamides as novel anti-inflammatory agents

  摘要：

  Triaylsulfonamides were identified as novel anti-inflammatory agents, acting by inhibition of RANKL and TNF alpha signaling. Structure-activity studies led to the identification of compounds with in vitro potencies of <100 nM against J774 macrophages and osteoclasts, but with little activity against osteoblasts or hepatocytes (IC50 >50 mu M). A representative compound (4k, ABD455) was able to completely prevent inflammation in vivo in a prevention model and was highly effective at controlling inflammation in a treatment model. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.067
• 作为产物：
  描述：

  间氨基苯甲酸 在 吡啶 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 ethyl 3-((4-bromophenyl)sulfonamido)benzoate
  参考文献：
  名称：

  Development of triarylsulfonamides as novel anti-inflammatory agents

  摘要：

  Triaylsulfonamides were identified as novel anti-inflammatory agents, acting by inhibition of RANKL and TNF alpha signaling. Structure-activity studies led to the identification of compounds with in vitro potencies of <100 nM against J774 macrophages and osteoclasts, but with little activity against osteoblasts or hepatocytes (IC50 >50 mu M). A representative compound (4k, ABD455) was able to completely prevent inflammation in vivo in a prevention model and was highly effective at controlling inflammation in a treatment model. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.067

文献信息

• Sulfonamide Inhibitors of β‐Catenin Signaling as Anticancer Agents with Different Output on c‐MYC
  作者：Laura Di Magno、Fiorella Di Pastena、Michela Puxeddu、Giuseppe La Regina、Antonio Coluccia、Alessia Ciogli、Simone Manetto、Marella Maroder、Gianluca Canettieri、Romano Silvestri、Marianna Nalli

  DOI：10.1002/cmdc.202000594

  日期：2020.12.3

  The Wnt/β‐catenin pathway is often found deregulated in cancer. The aberrant accumulation of β‐catenin in the cell nucleus results in the development of various malignancies. Specific drugs against this signaling pathway for clinical treatments have not been approved yet. Herein we report inhibitors of β‐catenin signaling of potential therapeutic value as anticancer agents. Ethyl 4‐((4‐(trifluorom

  Wnt/β-catenin 通路在癌症中经常被发现失调。β-连环蛋白在细胞核中的异常积累导致各种恶性肿瘤的发展。针对这一信号通路的特定药物尚未获批用于临床治疗。在此，我们报告了具有潜在治疗价值的 β-catenin 信号抑制剂作为抗癌剂。Ethyl 4-((4-(trifluoromethyl)phenyl)sulfonamido)benzoate（化合物14）抑制对 Wnt 报告基因的影响，IC 50值为 7.0 μM，显着降低 c-MYC 水平，抑制 HCT116 结肠癌细胞生长（IC 50 20.2 μM)，不违反 Lipinski 和 Veber 规则，并显示预测的 Caco-2 和 MDCK 细胞通透性P app > 500 nm s-1。化合物14似乎具有开发新抗癌疗法的潜力。
• [EN] ARYL-PHENYL-SULFONAMIDE-PHENYLENE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS ARYL-PHÉNYL-SULFONAMINO-PHÉNYLÈNE ET LEURS UTILISATIONS
  申请人：PIMCO 2664 LTD

  公开号：WO2010032010A1

  公开（公告）日：2010-03-25

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl-phenyl-sulfonamido-phenylene compounds of the following formula (I) (collectively referred to herein as "APSAP compounds"). 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, in treatment, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activity in rheumatoid arthritis, osteoporosis, cancer-associated bone disease, Paget's disease and the like, etc.; and of cancer, such as a haematological malignancy, a solid tumour, etc.

  本发明通常涉及治疗化合物领域，更具体地涉及以下式(I)的某些芳基苯磺酰胺基苯基化合物（以下统称为“APSAP化合物”）。本发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在体内外的使用，例如用于治疗炎症和/或关节破坏和/或骨质流失；过度和/或不适当和/或持续激活免疫系统的疾病；炎症性和自身免疫性疾病，例如类风湿关节炎、牛皮癣、银屑病性关节炎、慢性阻塞性肺病（COPD）、动脉粥样硬化、炎症性肠病、强直性脊柱炎等；与骨质流失相关的疾病，例如类风湿性关节炎中与过度破骨细胞活性相关的骨质流失、骨质疏松症、癌症相关骨病、帕吉特病等；以及癌症，如血液系统恶性肿瘤、实体肿瘤等。
• Aryl-Phenyl-Sulfonamide-Phenylene Compounds and Their Use
  申请人：Greig Iain Robert

  公开号：US20110190302A1

  公开（公告）日：2011-08-04

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl-phenyl-sulfonamido-phenylene compounds of the following formula (I) (collectively referred to herein as “APSAP compounds”). 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, in treatment, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activity in rheumatoid arthritis, osteoporosis, cancer-associated bone disease, Paget's disease and the like, etc.; and of cancer, such as a haematological malignancy, a solid tumour, etc.

  本发明涉及治疗化合物领域，更具体地涉及以下公式（I）的某些芳基-苯基-磺酰胺基-苯基化合物（以下统称为“APSAP化合物”）。本发明还涉及包含这些化合物的制药组合物，以及这些化合物和组合物的使用，无论是在体外还是体内，用于治疗炎症和/或关节破坏和/或骨质流失；治疗由免疫系统过度和/或不适当和/或持续激活引起的疾病；治疗炎症和自身免疫性疾病，例如类风湿性关节炎、牛皮癣、银屑病性关节炎、慢性阻塞性肺疾病（COPD）、动脉粥样硬化、炎性肠病、强直性脊柱炎等；治疗与骨质流失有关的疾病，例如类风湿关节炎中过度破骨细胞活动引起的骨质流失、骨质疏松症、癌症相关骨病、帕吉特病等；以及治疗癌症，例如血液系统恶性肿瘤、实体瘤等。
• Biphenyl-4-yl-sulfonic acid arylamides and their use as therapeutic agents
  申请人：Greig Iain Robert

  公开号：US20100286266A1

  公开（公告）日：2010-11-11

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl sulfonamides and related compounds (collectively referred to herein as ‘BPSAAA compounds’), as described herein, and including, for example, biphenyl-4-sulfonic acid (hydroxyalkyl-phenyl)-amides and related compounds. 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, in treatment and/or prevention, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of, inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activation in rheumatoid arthritis, osteoporosis, cancer associated bone disease, Paget's disease and the like.

  本发明涉及治疗化合物领域，更具体地涉及某些芳基磺酰胺和相关化合物（统称为“BPSAAA化合物”），如本文所述，包括例如联苯基-4-磺酸（羟基烷基-苯基）-酰胺和相关化合物。本发明还涉及包含这些化合物的制药组合物，以及这些化合物和组合物在体内外治疗和/或预防炎症、关节破坏和/或骨质流失等方面的使用，包括过度和/或不适当和/或持续激活免疫系统介导的疾病，炎症和自身免疫性疾病，例如类风湿性关节炎、银屑病、银屑病性关节炎、慢性阻塞性肺疾病（COPD）、动脉粥样硬化、炎症性肠病、强直性脊柱炎等，以及与骨质流失相关的疾病，例如类风湿性关节炎中过度成骨破骨细胞激活、骨质疏松症、癌症相关骨病、帕吉特病等。
• BIPHENYL-4-YL-SULFONIC ACID ARYLAMIDES AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：The University Court of The University of Aberdeen

  公开号：EP2137141B1

  公开（公告）日：2015-12-02