2-acetamido-5-benzyl thiophene | 190966-96-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-acetamido-5-benzyl thiophene
• 英文别名: N-(5-benzylthiophen-2-yl)acetamide
• CAS: 190966-96-2
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: KTBLWAMCGQPNTO-UHFFFAOYSA-N

物化性质

• 沸点：
  422.3±33.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetamido-5-benzyl thiophene 在 ammonium hydroxide 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 1.75h， 生成 2-methane-sulfonamido-5-benzyl thiophene
  参考文献：
  名称：

  N-(5-substituted) thiophene-2-alkylsulfonamides as potent inhibitors of 5-lipoxygenase

  摘要：

  Compound 4k N-[5-(4-fluoro) phenoxythien-2-yl] methanesulfonamide is representative of a new class of potent inhibitors of 5-lipoxygenase (5-LO). These versatile compounds exhibit dose-dependent inhibition of 5-LO with IC(50)s ranging from 20-100 nM in the rat basophilic leukemia (RBL-1) cell homogenate assay and submicromolar IC,,s in both the RBL-1 and human peripheral blood leukocyte (PBL) whole cell assays. Compound 4k also showed significant anti-inflammatory activity in the adjuvant arthritic rat at an oral dose of 3 mg/kg. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00025-4
• 作为产物：
  描述：

  5-硝基噻吩-2-甲醛 在 三乙基硅烷 、 三氟化硼乙醚 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-acetamido-5-benzyl thiophene
  参考文献：
  名称：

  N-(5-substituted) thiophene-2-alkylsulfonamides as potent inhibitors of 5-lipoxygenase

  摘要：

  Compound 4k N-[5-(4-fluoro) phenoxythien-2-yl] methanesulfonamide is representative of a new class of potent inhibitors of 5-lipoxygenase (5-LO). These versatile compounds exhibit dose-dependent inhibition of 5-LO with IC(50)s ranging from 20-100 nM in the rat basophilic leukemia (RBL-1) cell homogenate assay and submicromolar IC,,s in both the RBL-1 and human peripheral blood leukocyte (PBL) whole cell assays. Compound 4k also showed significant anti-inflammatory activity in the adjuvant arthritic rat at an oral dose of 3 mg/kg. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00025-4

文献信息

• 2,5-disubstituted thiophenes: inhibitors of 5-lipoxygenase and inducible
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05783597A1

  公开（公告）日：1998-07-21

  2,5-Disubstituted thiophene derivatives, and more particularly, to 2-aryloxy-5-alkansulfonamido-thiophenes of the general formula: ##STR1## Wherein, R.sub.2 is CF.sub.3, C.sub.1 -C.sub.10 alkyl, or phenyl; X is O, S, or CH.sub.2 ; and R is aryl, C.sub.1 -C.sub.10 alkyl, or C.sub.3 -C.sub.8 cycloalkyl; which compounds are pharmacologically active in alleviating inflammation, asthma, arthritis, hypersensitivity, myocardial ischemia and dermatological conditions, such as, psoriasis and dermatitis, and gastrointestinal inflammatory conditions, such as, inflammatory bowel syndrome.

  本发明涉及2,5-二取代噻吩衍生物，更具体地，涉及通式为：##STR1##的2-芳氧基-5-烷基磺酰胺基噻吩。其中，R.sub.2为CF.sub.3，C.sub.1-C.sub.10烷基或苯基；X为O，S或CH.sub.2；R为芳基，C.sub.1-C.sub.10烷基或C.sub.3-C.sub.8环烷基。这些化合物在缓解炎症、哮喘、关节炎、过敏、心肌缺血和皮肤病（如牛皮癣和皮炎）以及胃肠道炎症状况（如炎性肠病）方面具有药理活性。
• US5783597A
  申请人：——

  公开号：US5783597A

  公开（公告）日：1998-07-21
• N-(5-substituted) thiophene-2-alkylsulfonamides as potent inhibitors of 5-lipoxygenase
  作者：Scott A. Beers、Elizabeth A. Malloy、Wei Wu、Michael Wachter、Justin Ansell、Monica Singer、Michele Steber、Arminda Barbone、Thomas Kirchner、David Ritchie、Dennis Argentieri

  DOI：10.1016/s0968-0896(97)00025-4

  日期：1997.4

  Compound 4k N-[5-(4-fluoro) phenoxythien-2-yl] methanesulfonamide is representative of a new class of potent inhibitors of 5-lipoxygenase (5-LO). These versatile compounds exhibit dose-dependent inhibition of 5-LO with IC(50)s ranging from 20-100 nM in the rat basophilic leukemia (RBL-1) cell homogenate assay and submicromolar IC,,s in both the RBL-1 and human peripheral blood leukocyte (PBL) whole cell assays. Compound 4k also showed significant anti-inflammatory activity in the adjuvant arthritic rat at an oral dose of 3 mg/kg. (C) 1997 Elsevier Science Ltd.