4-(3-Methyl-ureido)-benzenesulfonyl chloride | 677326-97-5

• 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-(3-Methyl-ureido)-benzenesulfonyl chloride
• 英文别名: 4-(methylcarbamoylamino)benzenesulfonyl chloride
• CAS: 677326-97-5
• 化学式: C₈H₉ClN₂O₃S
• mdl: MFCD03424861
• 分子量: 248.69
• InChiKey: AUVKUNSZASYBOE-UHFFFAOYSA-N

物化性质

• 熔点：
  122°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-Methyl-ureido)-benzenesulfonyl chloride 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 N-(4-{2-[(S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenyl)-4-(3-methyl-ureido)-benzenesulfonamide
  参考文献：
  名称：

  Discovery of L-755,507: A subnanomolar human β3 adrenergic receptor agonist

  摘要：

  A study of 4-acylaminobenzenesulfonamides in a cloned human beta(3) adrenergic receptor assay resulted in the discovery of n-hexylurea, L-755,507 (22). This 0.43 nM beta(3) agonist, which is > 440-fold selective over both beta(1) and beta(2) binding, is among the most potent human beta(3) agonists reported to date. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00170-x
• 作为产物：
  描述：

  4-(氯磺酰)异氰酸苯酯 、 甲胺 以 四氢呋喃 为溶剂， 生成 4-(3-Methyl-ureido)-benzenesulfonyl chloride
  参考文献：
  名称：

  Design and synthesis of procollagen C-proteinase inhibitors

  摘要：

  Non-peptidic inhibitors of procollagen C-proteinase (PCP) were designed from substrate leads. Compounds were optimized for potency and selectivity, with N-substituted aryl sulfonamide hydroxamates having the best combination of these properties. Compounds 89 and 60 have IC50 values of 10 and 80 nM, respectively, against PCP; excellent selectivity over MMP's 1, 2, and 9; and activity in cell-based collagen deposition assays. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.067

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF<br/>[FR] DERIVES DE BENZIMIDAZOLE, COMPOSITIONS LES CONTENANT, PREPARATION DE CES COMPOSITIONS ET UTILISATIONS CORRESPONDANTES
  申请人：ASTRAZENECA AB

  公开号：WO2005030761A1

  公开（公告）日：2005-04-07

  Compounds of Formula (I) or pharmaceutically acceptable salts thereof; wherein R1, R2, R3, R4, n and Ar are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  化合物的分子式（I）或其药用盐；其中R1、R2、R3、R4、n和Ar的定义如规范中所述，以及包括这些化合物的盐和药物组合物已经准备好。它们在治疗中很有用，特别是在疼痛管理方面。
• Benzimidazole derivatives compositions containing them, preparation thereof and uses thereof
  申请人：Liu Ziping

  公开号：US20070072853A1

  公开（公告）日：2007-03-29

  Compounds of Formula (I) or pharmaceutically acceptable salts thereof; wherein R 1 , R 2 , R 3 , R 4 , n and Ar are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  本发明涉及公式（I）的化合物或其药学上可接受的盐；其中R1，R2，R3，R4，n和Ar如规范中所定义，以及制备包括这些化合物的盐和药物组合物。它们在治疗方面有用，特别是在疼痛管理方面。
• Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
  申请人：Page Daniel

  公开号：US20070082899A1

  公开（公告）日：2007-04-12

  Compounds of Formulae (IA), (IB) or pharmaceutically acceptable salts thereof; wherein Het, X 1 , R 1 , R 2 , R 3 , R 3 a and R 4 are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  本发明提供了化合物的公式（IA）、（IB）或其药学上可接受的盐；其中Het、X1、R1、R2、R3、R3a和R4如规范中所定义，并制备了包括这些化合物的盐和药物组合物。它们在治疗中有用，特别是在疼痛管理方面。
• 1,2,4-Oxadiazole derivatives targeting EGFR and c-Met degradation in TKI resistant NSCLC
  作者：Eman M.E. Dokla、Chun-Sheng Fang、Khaled A.M. Abouzid、Ching S. Chen

  DOI：10.1016/j.ejmech.2019.111607

  日期：2019.11

  Development of small-molecule agents with the ability to facilitate oncoprotein degradation has emerged as a promising strategy for cancer therapy. Since EGFR and c-Met are both implicated in oncogenesis and tumor progression, we initiated a screening program by using an in-house library to identify agents capable of inducing the concomitant suppression of EGFR and c-Met expression, which led to the identification of compound 1, a 1,2,4-oxadiazole derivative. Based on the scaffold of 1, we developed a series of derivatives to assess their efficacies in facilitating the downregulation of EGFR and c-Met, among which compound 48 represented the optimal agent. 48 showed equipotent anti-proliferative activity against a panel of five NSCLC cell lines with different EGFR mutational status (IC50 = 0.2-0.6 mu M), while the same panel exhibited differential sensitivity to different EGFR kinase inhibitors tested. Cell cycle analysis indicated that the antiproliferative activity of 48 was associated with its ability to cause G2/M arrest and, to a lesser extent, apoptosis. Western blot and RT-PCR analyses revealed that 48 facilitated the downregulation of EGFR and c-Met at the protein level. In vivo data showed that oral administration of 48 was effective in suppressing gefitinib-resistant H1975 xenograft tumor growth in nude mice, and at a suboptimal dose, could sensitize H1975 tumors to gefitinib. Based on these findings, 48 represents a promising candidate for further development to target EGFR TKI-resistant NSCLC via dual inhibition of EGFR and c-Met oncoproteins. (C) 2019 Elsevier Masson SAS. All rights reserved.
• 3-pyridylethanolamines: Potent and selective human β3 adrenergic receptor agonists
  作者：Elizabeth M. Naylor、Vincent J. Colandrea、Mari R. Candelore、Margaret A. Cascieri、Lawrence F. Colwell、Liping Deng、William P. Feeney、Michael J. Forrest、Gary J. Hom、D. Euan MacIntyre、Catherine D. Strader、Laurie Tota、Pei-Ran Wang、Matthew J. Wyvratt、Michael H. Fisher、Ann E. Weber

  DOI：10.1016/s0960-894x(98)00571-x

  日期：1998.11

  The 3-pyridylethanolamine L-757,793 is a potent beta(3) AR agonist (EC50 6.3 nM, 70% activation) with 1,300- and 500-fold selectivity over binding to the beta(1) and beta(2) ARs, respectively. L-757,793 stimulated lipolysis in rhesus monkeys (ED50 0.2 mg/kg) with a maximum response equivalent to that elicited by isoproterenol. (C) 1998 Elsevier Science Ltd. All rights reserved.