4-bromo-2,5-dimethylbenzenesulfonyl chloride | 14207-30-8

• 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-2,5-dimethylbenzenesulfonyl chloride
• 英文别名: 4-Bromo-2,5-dimethylbenzene-1-sulfonyl chloride
• CAS: 14207-30-8
• 化学式: C₈H₈BrClO₂S
• mdl: MFCD14702910
• 分子量: 283.573
• InChiKey: NTZAPNSSTHUFND-UHFFFAOYSA-N

物化性质

• 熔点：
  55 °C
• 沸点：
  140 °C(Press: 2 Torr)
• 密度：
  1.622±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  4-bromo-2,5-dimethylbenzenesulfonyl chloride 在 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Discovery of Novel Potent and Highly Selective Glycogen Synthase Kinase-3β (GSK3β) Inhibitors for Alzheimer’s Disease: Design, Synthesis, and Characterization of Pyrazines

  摘要：

  Glycogen synthase kinase-3 beta, also called tau phosphorylating kinase, is a proline-directed serine/threonine kinase which was originally identified due to its role in glycogen metabolism. Active forms of GSK3 beta localize to pretangle pathology including dystrophic neuritis and neurofibrillary tangles in Alzheimer's disease (AD) brain. By using a high throughput screening (HTS) approach to search for new chemical series and cocrystallization of key analogues to guide the optimization and synthesis of our pyrazine series, we have developed highly potent and selective inhibitors showing cellular efficacy and blood-brain barrier penetrance. The inhibitors are suitable for in vivo efficacy testing and may serve as a new treatment strategy for Alzheimer's disease.

  DOI：

  10.1021/jm201724m
• 作为产物：
  描述：

  甲苄基溴 在 氯磺酸 作用下， 以 氯仿 为溶剂， 反应 4.5h， 以90%的产率得到4-bromo-2,5-dimethylbenzenesulfonyl chloride
  参考文献：
  名称：

  基于过度拥挤烯烃的双功能分子光开关用于动态控制迈克尔加成反应中的催化活性

  摘要：

  新兴的人工光开关催化领域最近展示了功能性光响应系统的惊人例子，允许动态控制有机催化和金属催化转化中的活性和选择性。虽然我们小组已经公开了以第一代分子马达作为可切换中心核心的系统，但缺乏基于第二代分子马达的设计。在这里，报道了基于光响应性四取代烯烃核心的两个双功能化分子开关的合成。它们在上半部分具有硫脲取代基作为供氢部分，在下半部分具有碱性二甲胺基团。这种官能团的组合为这些分子在光可切换催化过程中的应用提供了可能性。通过预功能化的上半部和下半部的 Barton-Kellogg 耦合合成光响应中心核。使用 Buchwald-Hartwig 胺化和随后引入硫脲取代基的衍生化得到目标化合物。控制迈克尔加成反应中的催化活性（E )-3-溴-β-硝基苯乙烯和2,4-戊二酮是在双功能催化剂1的稳定-( E )和稳定-( Z )异构体的辐照下得到的。两种异构体在辐照到亚稳态后都表现出催化活性的降低，为系统提供了用作开/关催化光开关的潜力。

  DOI：

  10.1002/chem.201604966

文献信息

• Chemical Compounds
  申请人：Greener Benjamin Scott

  公开号：US20130109696A1

  公开（公告）日：2013-05-02

  The invention relates to sulfonamide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to new sulfonamide Nav1.7 inhibitors of formula (I) or pharmaceutically acceptable salts thereof, wherein X, Y 1 , Y 2 , Z, R 1 , R 2 and R 3 are as defined in the description. Nav 1.7 inhibitors are potentially useful in the treatment of a wide range of disorders, particularly pain.

  本发明涉及磺酰胺衍生物及其在医药中的应用，包括含有它们的组合物、制备它们的方法以及用于这些方法的中间体。更具体地说，本发明涉及一种新的磺酰胺Nav1.7抑制剂，其化学式为(I)或其药学上可接受的盐，其中X、Y1、Y2、Z、R1、R2和R3在说明书中有定义。Nav 1.7抑制剂在治疗广泛的疾病中具有潜在的用途，特别是在疼痛治疗方面。
• Synthesis and structure–activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3
  作者：Daniel M. Heinrich、Jack U. Flanagan、Stephen M.F. Jamieson、Shevan Silva、Laurent J.M. Rigoreau、Elisabeth Trivier、Tony Raynham、Andrew P. Turnbull、William A. Denny

  DOI：10.1016/j.ejmech.2013.01.047

  日期：2013.4

  High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (<100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• [EN] NEMATOCIDAL SULFONAMIDES<br/>[FR] SULFONAMIDES NÉMATOCIDES
  申请人：DU PONT

  公开号：WO2010129500A3

  公开（公告）日：2011-01-06
• Cagniant,P. et al., Bulletin de la Societe Chimique de France, 1966, p. 3055 - 3065
  作者：Cagniant,P. et al.

  DOI：——

  日期：——
• US9096558B2
  申请人：——

  公开号：US9096558B2

  公开（公告）日：2015-08-04