2-(2-butyramido-ethyl)-thiophene | 55694-78-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(2-butyramido-ethyl)-thiophene
• 英文别名: N-(2-thiophen-2-ylethyl)butanamide
• CAS: 55694-78-5
• 化学式: C₁₀H₁₅NOS
• mdl: MFCD00207707
• 分子量: 197.301
• InChiKey: XBSOPBFKIMIRFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-(2-butyramido-ethyl)-thiophene 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 N-phenyl-4-propyl-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide
  参考文献：
  名称：

  Fused Piperidines as a Novel Class of Potent and Orally Available Transient Receptor Potential Melastatin Type 8 (TRPM8) Antagonists

  摘要：

  The transient receptor potential melastatin type 8 (TRPM8) is a nonselective cation channel primarily expressed in a subpopulation of sensory neurons that can be activated by a wide range of stimuli, including menthol, icilin, and cold temperatures (< 25 degrees C). Antagonism of TRPM8 is currently under investigation as a new approach for the treatment of pain. As a result of our screening efforts, we identified tetrahydrothienopyridine 4 as an inhibitor of icilin-induced calcium influx in CHO cells expressing recombinant rat TRPM8. Exploration of the structure-activity relationships of 4 led to the identification of a potent and orally bioavailable TRPM8 antagonist, tetrahydroisoquinoline 87. Compound 87 demonstrated target coverage in vivo after oral administration in a rat pharmacodynamic model measuring the prevention of icilin-induced wet-dog shakes (WDS).

  DOI：

  10.1021/jm2013634
• 作为产物：
  描述：

  噻吩乙胺 、 丁酰氯 在 盐酸 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 生成 2-(2-butyramido-ethyl)-thiophene
  参考文献：
  名称：

  1-Heteroarylsulphonyl-2-imino-imidazolidines

  摘要：

  1-杂环磺酰基-2-亚胺-咪唑啉类化合物，其在3位被脂肪或环脂烃基取代，特别是环烷基基团，以及它们的药学上可接受的酸盐具有宝贵的药理学性质。特别是，它们具有降糖活性，可用于治疗哺乳动物的高血糖。一个具体的实施例是1-[5-(2-丁酰胺基乙基)-2-噻吩基磺酰基]-2-亚胺-5-环己基咪唑啉。

  公开号：

  US03941804A1

文献信息

• COMPOUNDS FOR THE TREATMENT OF CANCER AND INFLAMMATORY DISEASE
  申请人：SHY Therapeutics LLC

  公开号：US20170174699A1

  公开（公告）日：2017-06-22

  Provided herein are compounds that inhibit the phosphorylation of MAPK and thus are useful in compositions and methods for treating cancer and inflammatory disease.

  本文提供了抑制MAPK磷酸化的化合物，因此可用于治疗癌症和炎症性疾病的组合物和方法。
• 1-Heteroarylsulphonyl-2-imino-imidazolidines
  申请人：Ciba-Geigy Corporation

  公开号：US03941804A1

  公开（公告）日：1976-03-02

  Compounds of the class of 1-heteroarylsulphonyl-2-imino-imidazolidines which are substituted in the 3-position by an aliphatic or cycloaliphatic hydrocarbon radical, especially a cycloalkyl radical, and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties. In particular, they possess hypoglycaemic activity and can be used for the treatment of hyperglycaemia in mammals. A specific embodiment is 1-[5-(2-butyramido-ethyl)-2-thienylsulphonyl]-2-imino-5-cyclohexyl-imidazo lidine.

  1-杂环磺酰基-2-亚胺-咪唑啉类化合物，其在3位被脂肪或环脂烃基取代，特别是环烷基基团，以及它们的药学上可接受的酸盐具有宝贵的药理学性质。特别是，它们具有降糖活性，可用于治疗哺乳动物的高血糖。一个具体的实施例是1-[5-(2-丁酰胺基乙基)-2-噻吩基磺酰基]-2-亚胺-5-环己基咪唑啉。
• US3941804A
  申请人：——

  公开号：US3941804A

  公开（公告）日：1976-03-02
• Fused Piperidines as a Novel Class of Potent and Orally Available Transient Receptor Potential Melastatin Type 8 (TRPM8) Antagonists
  作者：Nuria A. Tamayo、Yunxin Bo、Vijay Gore、Vu Ma、Nobuko Nishimura、Phi Tang、Hong Deng、Lana Klionsky、Sonya G. Lehto、Weiya Wang、Brad Youngblood、Jiyun Chen、Tiffany L. Correll、Michael D. Bartberger、Narender R. Gavva、Mark H. Norman

  DOI：10.1021/jm2013634

  日期：2012.2.23

  The transient receptor potential melastatin type 8 (TRPM8) is a nonselective cation channel primarily expressed in a subpopulation of sensory neurons that can be activated by a wide range of stimuli, including menthol, icilin, and cold temperatures (< 25 degrees C). Antagonism of TRPM8 is currently under investigation as a new approach for the treatment of pain. As a result of our screening efforts, we identified tetrahydrothienopyridine 4 as an inhibitor of icilin-induced calcium influx in CHO cells expressing recombinant rat TRPM8. Exploration of the structure-activity relationships of 4 led to the identification of a potent and orally bioavailable TRPM8 antagonist, tetrahydroisoquinoline 87. Compound 87 demonstrated target coverage in vivo after oral administration in a rat pharmacodynamic model measuring the prevention of icilin-induced wet-dog shakes (WDS).