methyl (E)-3-[3-fluoro-4-(methylsulfonamido)phenyl]acrylate | 1165739-17-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-[3-fluoro-4-(methylsulfonamido)phenyl]acrylate
• 英文别名: methyl (E)-3-[3-fluoro-4-(methanesulfonamido)phenyl]prop-2-enoate
• CAS: 1165739-17-2
• 化学式: C₁₁H₁₂FNO₄S
• 分子量: 273.285
• InChiKey: SZNBQVATIVUJOU-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[3-fluoro-4-(methylsulfonamido)phenyl]acrylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到methyl 3-{3-fluoro-4-[(methanesulfony)amino]phenyl}propanoate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists

  摘要：

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.010
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 N-(2-fluoro-4-iodophenyl)methanesulfonamide 在 1,1'-bis(diphenylphosphino)ferrocene 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以91%的产率得到methyl (E)-3-[3-fluoro-4-(methylsulfonamido)phenyl]acrylate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists

  摘要：

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.010

文献信息

• Novel thiourea derivatives and the pharmaceutical compositions containing the same
  申请人：Suh Ger Young

  公开号：US20080064687A1

  公开（公告）日：2008-03-13

  The present invention relates to novel thiourea derivatives as a modulator for vanilloid receptor (VR) and the pharmaceutical compositions containing the same. As diseases associated with the activity of vanilloid receptor, pain acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflammatory bowel disease and inflammatory diseases can be enumerated. The present invention provides a pharmaceutical composition for prevention or treatment of these diseases.

  本发明涉及一种新型硫脲衍生物，作为vanilloid受体（VR）的调节剂，并包含相应的药物组合物。作为与vanilloid受体活动相关的疾病，可以列举急性疼痛、慢性疼痛、神经病性疼痛、术后疼痛、偏头痛、关节痛、神经病、神经损伤、糖尿病神经病变、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合征、哮喘或慢性阻塞性肺疾病、皮肤、眼睛或黏膜刺激、发热、胃十二指肠溃疡、炎症性肠病和炎症性疾病等。本发明提供了一种用于预防或治疗这些疾病的药物组合物。
• US8071650B2
  申请人：——

  公开号：US8071650B2

  公开（公告）日：2011-12-06
• Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists
  作者：Fu-Nan Li、Nam-Jung Kim、Seung-Mann Paek、Do-Yeon Kwon、Kyung Hoon Min、Yeon-Su Jeong、Sun-Young Kim、Young-Ho Park、Hee-Doo Kim、Hyeung-Geun Park、Young-Ger Suh

  DOI：10.1016/j.bmc.2009.04.010

  日期：2009.5

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.