4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride | 201470-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride
• 英文别名: 4-(3-octyl-2-oxoimidazolidin-1-yl)benzenesulfonyl chloride
• CAS: 201470-20-4
• 化学式: C₁₇H₂₅ClN₂O₃S
• 分子量: 372.916
• InChiKey: YHXCWMWAKARJLV-UHFFFAOYSA-N

物化性质

• 沸点：
  481.4±47.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-{4-[2-(2-Hydroxy-2-pyridin-3-yl-ethylamino)-ethyl]-phenyl}-4-(3-octyl-2-oxo-imidazolidin-1-yl)-benzenesulfonamide
  参考文献：
  名称：

  Human β3 adrenergic receptor agonists containing cyclic ureidobenzenesulfonamides

  摘要：

  Human beta(3) adrenergic receptor agonists containing 5-membered ring ureas were shown to be potent partial agonists with excellent selectivity over beta(1) and beta(2) binding. L-760,087 (4a) and L-764,646 (5a) (beta(3) EC50 = 18 and 14 nM, respectively) stimulate lipolysis in rhesus monkeys (ED50 = 0.2 and 0.1 mg/kg, respectively) with minimal effects on heart rate. Oral absorption in dogs is improved over other urea analogs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00073-6
• 作为产物：
  描述：

  1-(2-氯乙基)-3-苯基脲 在 氯磺酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride
  参考文献：
  名称：

  Human β3 adrenergic receptor agonists containing cyclic ureidobenzenesulfonamides

  摘要：

  Human beta(3) adrenergic receptor agonists containing 5-membered ring ureas were shown to be potent partial agonists with excellent selectivity over beta(1) and beta(2) binding. L-760,087 (4a) and L-764,646 (5a) (beta(3) EC50 = 18 and 14 nM, respectively) stimulate lipolysis in rhesus monkeys (ED50 = 0.2 and 0.1 mg/kg, respectively) with minimal effects on heart rate. Oral absorption in dogs is improved over other urea analogs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00073-6

文献信息

• Substituted sulfonamides as selective .beta.-3 agonists for the
  申请人：Merck & Co., Inc.

  公开号：US05705515A1

  公开（公告）日：1998-01-06

  Substituted sulfonamides are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.

  替代磺酰胺是高度选择性的β3肾上腺素受体激动剂，几乎没有β1和β2肾上腺素受体活性，因此这些化合物能够增加细胞内脂解和能量消耗。这些化合物因此在治疗II型糖尿病和肥胖症方面具有强大的活性。这些化合物也可以用于降低甘油三酯水平和胆固醇水平，或提高高密度脂蛋白水平，或减少肠道蠕动。此外，这些化合物还可以用于减少神经源性炎症或作为抗抑郁剂。这些化合物通过将氨基烷基苯磺酰胺与适当取代的环氧化物偶联而制备。还公开了使用这些化合物治疗糖尿病和肥胖症，降低甘油三酯水平和胆固醇水平或提高高密度脂蛋白水平或增加肠道蠕动的组合物和方法。
• Homologation of the Alkyl Side Chain of Antimitotic Phenyl 4-(2-Oxo-3-alkylimidazolidin-1-yl)benzenesulfonate Prodrugs Selectively Targeting CYP1A1-Expressing Breast Cancers Improves Their Stability in Rodent Liver Microsomes
  作者：Atziri Corin Chavez Alvarez、Chahrazed Bouzriba、Emmanuel Moreau、Philippe Auzeloux、Sophie Besse、Vincent Ouellette、Mitra Zarifi Khosroshahi、Marie-France Côté、Sylvie Pilote、Elisabeth Miot-Noirault、Jean-Michel Chezal、Chantale Simard、René C -Gaudreault、Sébastien Fortin

  DOI：10.1021/acs.jmedchem.2c01268

  日期：2023.2.23

  Phenyl 4-(2-oxo-3-alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) are a new family of antimitotic prodrugs bioactivated in breast cancer cells expressing CYP1A1. In this study, we report that the 14C-labeled prototypical PAIB-SO [14C]CEU-818 and its antimitotic counterpart [14C]CEU-602 are distributed in whole mouse body and they show a short half-life in mice. To circumvent this limitation, we

  苯基 4-(2-oxo-3-alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) 是一个新的抗有丝分裂前药家族，在表达 CYP1A1 的乳腺癌细胞中被生物激活。在这项研究中，我们报告了14 C 标记的原型 PAIB-SO [ 14 C]CEU-818 及其抗有丝分裂对应物 [ 14 C]CEU-602 分布在整个小鼠体内，并且它们在小鼠体内的半衰期较短. 为了规避这一限制，我们评估了 PAIB-SOs 的咪唑啉-2-one 部分的烷基侧链同系化的影响。我们的研究表明，PAIB-SO 具有n-戊基侧链在纳摩尔到低微摩尔范围内表现出抗增殖活性，并且对 CYP1A1 阳性乳腺癌细胞具有高选择性。此外，最有效的正戊基 PAIB-SO 对啮齿动物肝微粒体的稳定性明显更高。此外，PAIB-SO 10和14在绒毛尿囊膜 (CAM) 测定中显示出显着的抗肿
• EP0915847A4
  申请人：——

  公开号：EP0915847A4

  公开（公告）日：2001-01-17
• SUBSTITUTED SULFONAMIDES AS SELECTIVE BETA3 AGONISTS FOR THE TREATMENT OF DIABETES AND OBESITY
  申请人：MERCK & CO., INC.

  公开号：EP0915847A1

  公开（公告）日：1999-05-19
• Substituted 2-Imidazolidinones and 2-Imidazolones and Their Use in the Treatment of Cancer
  申请人：C.-Gaudreault Rene

  公开号：US20140315968A1

  公开（公告）日：2014-10-23

  Compounds of formula (I) wherein R 1 , R 4 , R 8 , X and Y as defined herein are provided as useful for the inhibition of certain types of cancer cells, amongst others, breast cancer cells, or for the manufacture of anti-cancer agents.