4-(2-methyloxazol–5-yl)benzene-1-sulfonylchloride | 293306-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-methyloxazol–5-yl)benzene-1-sulfonylchloride
• 英文别名: 4-(2-Methyl-oxazol-5-yl)-benzenesulfonyl chloride；4-(2-Methyl-1,3-oxazol-5-yl)benzenesulfonyl chloride
• CAS: 293306-72-6
• 化学式: C₁₀H₈ClNO₃S
• mdl: MFCD18447678
• 分子量: 257.697
• InChiKey: ACSNDJTZQWNDQK-UHFFFAOYSA-N

物化性质

• 沸点：
  384.1±25.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-methyloxazol–5-yl)benzene-1-sulfonylchloride 在 吡啶 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-[4-[2-[[(2R)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]-4-(2-methyl-1,3-oxazol-5-yl)benzenesulfonamide
  参考文献：
  名称：

  Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists

  摘要：

  As a part of our investigation into the development of orally bioavailable beta(3) adrenergic receptor agonists, we have identified a series of substituted oxazole derivatives that are potent beta(3) agonists with excellent selectivity against other beta receptors. Several of these compounds showed excellent oral bioavailability in dogs. One example, cyclopentylethyloxazole 5f is a potent beta(3) agonist (EC50 = 14 nM, 84% activation) with 340-fold and 160-fold selectivity over beta(1) and beta(2) receptors, respectively, and has 38% oral bioavailability in dogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00277-8
• 作为产物：
  描述：

  2-甲基-5-苯基-噁唑 在 氯磺酸 、 氯化亚砜 作用下， 反应 2.0h， 生成 4-(2-methyloxazol–5-yl)benzene-1-sulfonylchloride
  参考文献：
  名称：

  1,3-Oxazole-based selective picomolar inhibitors of cytosolic human carbonic anhydrase II alleviate ocular hypertension in rabbits: Potency is supported by X-ray crystallography of two leads

  摘要：

  Two lead 1,3-oxazole-based carbonic anhydrase inhibitors (CAIs) earlier identified as selective, picomolar inhibitors of hCA II (a cytosolic target for treatment of glaucoma) have been investigated further. Firstly, they were found to be conveniently synthesized on multigram scale, which enables further development. These compounds were found to be comparable in efficacy to dorzolamide eye drops when applied in the eye drop form as well. Finally, the reasons for unusually high potency of these compounds became understood from their high-resolution X-ray crystallography structures. These data significantly expand our understanding of heterocycle-based primary sulfonamides, many of which have recently emerged from our labs - particularly, from the corneal permeability standpoint. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.054

文献信息

• Aryl sulfonamides
  申请人：Ungashe Solomon

  公开号：US20060111351A1

  公开（公告）日：2006-05-25

  Compounds are provided that act as potent antagonists of the CCR9 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR9. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR9-mediated diseases, and as controls in assays for the identification of CCR9 antagonists.

  提供了作为CCR9受体的有效拮抗剂的化合物，并在动物炎症测试中进一步确认了其效果，这是CCR9的标志性疾病状态之一。这些化合物通常是芳基磺酰胺衍生物，可用于制备药物组合物，治疗CCR9介导的疾病的方法，并作为CCR9拮抗剂鉴定的检测中的对照。
• ARYL SULFONAMIDES
  申请人：Ungashe Solomon

  公开号：US20120014997A1

  公开（公告）日：2012-01-19

  Compounds are provided that act as potent antagonists of the CCR9 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR9. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR9-mediated diseases, and as controls in assays for the identification of CCR9 antagonists.

  提供了一些化合物，它们作为CCR9受体的有效拮抗剂，并在动物炎症测试中得到进一步确认，这是CCR9的典型疾病状态之一。这些化合物通常是芳基磺酰胺衍生物，可用于制药组合物、CCR9介导疾病的治疗方法以及作为CCR9拮抗剂鉴定的检测控制。
• Aryl Sulfonamides
  申请人：Ungashe Solomon

  公开号：US20090163498A1

  公开（公告）日：2009-06-25

  Compounds are provided that act as potent antagonists of the CCR9 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR9. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR9-mediated diseases, and as controls in assays for the identification of CCR9 antagonists.

  提供了一些化合物，作为CCR9受体的有效拮抗剂，并已在动物炎症测试中进一步确认，这是CCR9的标志性疾病状态之一。这些化合物通常是芳基磺酰胺衍生物，并可用于制药组合物、治疗CCR9介导疾病的方法以及作为CCR9拮抗剂鉴定的检测控制。
• Probing the ‘bipolar’ nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms
  作者：Mikhail Krasavin、Mikhail Korsakov、Mikhail Dorogov、Tiziano Tuccinardi、Nurcan Dedeoglu、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2015.06.022

  日期：2015.8

  A series of potent inhibitors of human carbonic anhydrase (CA) isoforms I and II has been prepared via a direct, chemoselective sulfochlorination of a range of 1,3-oxazolyl benzenes and thiophenes, followed by primary sulfonamide synthesis. The latter functionality is a known zinc-binding group (ZBG) responsible for anchoring the inhibitors to the CA's zinc metal ion. The compound's periphery as well as the overall scaffold geometry was designed to enable optimal interactions with the two distinct sides of the enzyme's active site, one of which is lined with hydrophobic residues and while the other is predominantly hydrophilic. As a result, several compounds inhibiting the therapeutically important cytosolic CA I and CA II in picomolar range have been identified. These compounds are one of the most potent CA inhibitors identified to-date. Not only the remarkable (>10 000-fold), cytosolic CA I and CA II selectivity vs. the membrane-bound CA IX and CA XII isoforms, but also the pronounced CA II/I selectivity observed in some cases, allow considering this series as a set of isoform-selective chemical biology tools and promising starting points for drug candidate development. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US7420055B2
  申请人：——

  公开号：US7420055B2

  公开（公告）日：2008-09-02