N-(2-bromo-ethyl)-4-chloro-benzenesulfonamide | 151389-59-2

• 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: N-(2-bromo-ethyl)-4-chloro-benzenesulfonamide
• 英文别名: N-(2-bromoethyl)-4-chlorobenzenesulfonamide
• CAS: 151389-59-2
• 化学式: C₈H₉BrClNO₂S
• 分子量: 298.588
• InChiKey: RAHOHKTXDOPJHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-bromo-ethyl)-4-chloro-benzenesulfonamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 100.08h， 生成 Ethyl 3-bromo-2-[(4-chlorophenyl)sulfonyl-ethoxycarbonylamino]propanoate
  参考文献：
  名称：

  芳族磺酸盐和磺酰胺的微笑型自由基重排：芳基乙醇和芳基乙胺的合成。

  摘要：

  芳烃磺酸盐和芳烃磺酰胺的微笑型自由基重排用于合成目的。4-取代的苯磺酸盐仅在被吸电子基团取代时才引起Smiles型重排。因此，芳烷基磺酸盐上的烷基自由基引起的ipso攻击以亲电子方式发生。由于该基团的吸电子性，芳烃磺酰胺仅在酰胺氮被烷氧基羰基取代时才重排。萘，喹啉和噻吩的磺酸盐和N-乙氧基羰基磺酰胺衍生物引起更多的重排并显示出合成效用。通过Smiles型重排以中等产率合成芳族氨基酸类似物。

  DOI：

  10.1039/b303728b
• 作为产物：
  描述：

  2-溴乙胺 、 4-氯苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(2-bromo-ethyl)-4-chloro-benzenesulfonamide
  参考文献：
  名称：

  Identifying new lead structures to enhance tolerance towards drought stress via high-throughput screening giving crops a quantum of solace

  摘要：

  Novel synthetic lead structures interacting with RCAR/(PYR/PYL) receptor proteins were identified based on the results of a high-throughput screening campaign of a large compound library followed by focused SAR studies of the three most promising hit clusters. Whilst indolinylmethyl sulfonamides 8y,z and phenylsulfonyl ethylenediamines 9y,z showed strong affinities for RCAR/ (PYR/PYL) receptor proteins in wheat, thiotriazolyl acetamides 7f,s exhibited promising efficacy against drought stress in vivo (wheat, corn and canola) combined with confirmed target interaction in wheat and arabidopsis thaliana. Remarkably, binding affinities of several representatives of 8 and 9 were on the same level or even better than the essential plant hormone abscisic acid (ABA).

  DOI：

  10.1016/j.bmc.2019.115142

文献信息

• Carbazole-Containing Sulfonamides as Cryptochrome Modulators
  申请人：Reset Therapeutics, Inc.

  公开号：US20130303524A1

  公开（公告）日：2013-11-14

  The subject matter herein is directed to carbazole-containing sulfonamide derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, B, C, D, E, F, G, H, a, and b are accordingly described. Also provided are pharmaceutical compositions comprising the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, obesity, metabolic syndrome, Cushing's syndrome, and glaucoma.

  本文涉及含有咔唑基磺胺衍生物及其药用可接受盐或水合物的结构式I，其中变量R1、R2、R3、R4、R5、R6、R7、A、B、C、D、E、F、G、H、a和b分别描述。还提供了包含式I化合物的药物组合物，用于治疗Cry介导的疾病或紊乱，如糖尿病、肥胖症、代谢综合征、库欣综合征和青光眼。
• Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines <i>via</i> the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes
  作者：Mandala Anitha、K. C. Kumara Swamy

  DOI：10.1039/c7ob02915b

  日期：——

  Epoxy-sulfonamides react with heterocumulenes (carbon disulfide/isothiocyanates/isocyanates) in the presence of a base to afford ring expansion products in good to high yields with excellent regioselectivity. N-(2-Bromoethyl)-sulfonamides can also be employed as substrates. This reaction proceeds through a 5-exo-tet pathway without forming aziridine intermediates.

  环氧磺酰胺在碱的存在下与杂聚枯烯（二硫化碳/异硫氰酸酯/异氰酸酯）反应，以良好的收率和高收率提供极好的区域选择性的扩环产物。N-（2-溴乙基） -磺酰胺也可以用作底物。该反应通过5 -exo-tet途径进行，而没有形成氮丙啶中间体。
• Compounds
  申请人：Gore Paul Martin

  公开号：US20090270355A1

  公开（公告）日：2009-10-29

  The present invention relates to a compound which is N-(4-4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)ethanesulfonamide and salts thereof, processes for its preparation, to compositions containing it and to its use in the treatment of various diseases, such as allergic rhinitis.

  本发明涉及一种化合物，即N-(4-4-[(6-丁基-8-喹啉基)氧基]-1-哌啶基}丁基)乙烷磺酰胺及其盐，以及其制备方法、含有该化合物的组合物，以及在治疗各种疾病（如过敏性鼻炎）中的用途。
• Flexible diaminodihydrotriazine inhibitors of Plasmodium falciparum dihydrofolate reductase: Binding strengths, modes of binding and their antimalarial activities
  作者：Sumalee Kamchonwongpaisan、Netnapa Charoensetakul、Choladda Srisuwannaket、Supannee Taweechai、Roonglawan Rattanajak、Jarunee Vanichtanankul、Danoo Vitsupakorn、Uthai Arwon、Chawanee Thongpanchang、Bongkoch Tarnchompoo、Tirayut Vilaivan、Yongyuth Yuthavong

  DOI：10.1016/j.ejmech.2020.112263

  日期：2020.6

  and shown to inhibit P. falciparum dihydrofolate reductase (PfDHFR) of the wild type or those carrying either single (S108N), double (C59R + S108N and A16V + S108T), triple (N51I + C59R + S108N and C59R + S108N + I164L) or quadruple (N51I + C59R + S108N + I164L) mutations, responsible for antifolate resistance. The flexibility of the side chain at position N1 has been included in the design so as to avoid

  已开发出一系列灵活的二氨基二氢三嗪或环鸟嘌呤（Cyc）类似物，并显示可抑制野生型的恶性疟原虫二氢叶酸还原酶（PfDHFR）或携带单个（S108N），携带两个（C59R + S108N和A16V + S108T），携带三个（N51I + C59R + S108N和C59R + S108N + I164L）或四倍（N51I + C59R + S108N + I164L）突变，引起抗叶酸耐药性。设计中已包括位置N1的侧链的柔性，以避免与抗性突变体的残基108的侧链发生不利的空间相互作用。许多抑制剂对突变酶的抑制常数在低纳摩尔区域。用A16V和S108N系列突变体都实现了药物结合效率的重新获得。为与突变型酶最佳相互作用而设计的某些酶抑制剂复合物的X射线研究表明，结合模式与Ki值一致。这些化合物中的许多对具有突变酶的抗性恶性疟原虫显示出优异的抗疟活性，并且对哺乳动物细胞显示出低细胞毒性，使其成为抗疟药物的进一步开发的良好候选者。
• SUBSTITUTED QUINOLINE DERIVATIVES AS H1 RECEPTOR ANTAGONISTS
  申请人：Gore Paul Martin

  公开号：US20110281909A1

  公开（公告）日：2011-11-17

  The present invention relates to compounds of formula (I), and salts thereof, processes for their preparation, to compositions containing them and to their use in the treatment of various diseases, such as allergic rhinitis.

  本发明涉及公式（I）的化合物及其盐，其制备方法，含有它们的组合物以及它们在治疗各种疾病（如过敏性鼻炎）中的应用。