naphthalene-2-sulfonic acid (2-bromo-ethyl)-amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-2-sulfonic acid (2-bromo-ethyl)-amide
• 英文别名: N-(2-bromoethyl)naphthalene-2-sulfonamide
• 化学式: C₁₂H₁₂BrNO₂S
• 分子量: 314.203
• InChiKey: BBXQIULWYXWMQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  naphthalene-2-sulfonic acid (2-bromo-ethyl)-amide 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 {2-[2-(Naphthalene-2-sulfonylamino)-ethylsulfanyl]-thiazol-4-yl}-acetic acid
  参考文献：
  名称：

  Synthesis and activities of new arylsulfonamido thromboxane A2 receptor antagonists

  摘要：

  New benzoic, benzeneacetic and thiazole-4-acetic acids bearing an arylsulfonamido alkyl or alkylhetero side chain were synthesized and tested in vitro for affinity for human platelet thromboxane A2 receptors and inhibition of U46619-induced rat aortic ring contraction. Influence of substitution patterns, chain length and presence of heteroatoms were studied and compounds within a 30 nmol range for inhibition of U46619-induced contractions were found. One of the most potent, 2-[(4-chloro-benzenesulfonylamino-ethyl)thio] thiazole-4-acetic acid (VII-4) was orally active (1 mg/kg), as evidenced by the inhibition of U46619-induced platelet aggregation in guinea pigs, ex vivo.

  DOI：

  10.1016/0223-5234(93)90093-t
• 作为产物：
  描述：

  2-溴乙胺氢溴酸盐 、 2-萘磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 naphthalene-2-sulfonic acid (2-bromo-ethyl)-amide
  参考文献：
  名称：

  SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING MENTAL ILLNESS

  摘要：

  公开了一种硫酰胺衍生物及其作为活性成分用于预防或治疗精神疾病的药物组合物。所述衍生物在作为血清素、去甲肾上腺素和多巴胺的三重再摄取抑制剂方面非常有效，因此可用于有效地治疗精神疾病。

  公开号：

  EP4159718A1

文献信息

• 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。
• SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING MENTAL ILLNESS
  申请人：Daegu-Gyeongbuk Medical Innovation Foundation

  公开号：EP4159718A1

  公开（公告）日：2023-04-05

  Disclosed are a sulfonamide derivative and a pharmaceutical composition comprising same as an active ingredient for use in preventing or treating mental illness. The derivative is superbly effective in a triple reuptake inhibitor of serotonin, norepinephrine, and dopamine, and thus can be effectively used in treating mental illness.

  公开了一种硫酰胺衍生物及其作为活性成分用于预防或治疗精神疾病的药物组合物。所述衍生物在作为血清素、去甲肾上腺素和多巴胺的三重再摄取抑制剂方面非常有效，因此可用于有效地治疗精神疾病。
• Synthesis and activities of new arylsulfonamido thromboxane A2 receptor antagonists
  作者：E Sartori、F Camy、JM Teulon、F Caussade、A Virone-Oddos、A Cloarec

  DOI：10.1016/0223-5234(93)90093-t

  日期：1993.1

  New benzoic, benzeneacetic and thiazole-4-acetic acids bearing an arylsulfonamido alkyl or alkylhetero side chain were synthesized and tested in vitro for affinity for human platelet thromboxane A2 receptors and inhibition of U46619-induced rat aortic ring contraction. Influence of substitution patterns, chain length and presence of heteroatoms were studied and compounds within a 30 nmol range for inhibition of U46619-induced contractions were found. One of the most potent, 2-[(4-chloro-benzenesulfonylamino-ethyl)thio] thiazole-4-acetic acid (VII-4) was orally active (1 mg/kg), as evidenced by the inhibition of U46619-induced platelet aggregation in guinea pigs, ex vivo.
• In silico identification, design and synthesis of novel piperazine-based antiviral agents targeting the hepatitis C virus helicase
  作者：Marcella Bassetto、Pieter Leyssen、Johan Neyts、Mark M. Yerukhimovich、David N. Frick、Matthew Courtney-Smith、Andrea Brancale

  DOI：10.1016/j.ejmech.2016.10.043

  日期：2017.1

  A structure-based virtual screening of commercial compounds was carried out on the HCV NS3 helicase structure, with the aim to identify novel inhibitors of HCV replication. Among a selection of 13 commercial structures, one compound was found to inhibit the subgenomic HCV replicon in the low micromolar range. Different series of new piperazine-based analogues were designed and synthesised, and among them, several novel structures exhibited antiviral activity in the HCV replicon assay. Some of the new compounds were also found to inhibit HCV NS3 helicase function in vitro, and one directly bound NS3 with a dissociation constant of 570 +/- 270 nM. (C) 2016 Elsevier Masson SAS. All rights reserved.