2-[(E)-2-isocyanatoethenyl]thiophene | 76197-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-[(E)-2-isocyanatoethenyl]thiophene
• CAS: 76197-76-7
• 化学式: C₇H₅NOS
• 分子量: 151.189
• InChiKey: IRDNPBJUWDDPTF-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-aminopenicillanic acid trimethylsilyl ester 、 2-[(E)-2-isocyanatoethenyl]thiophene 在 sodium 2-ethylhexanoic acid 作用下， 生成
  参考文献：
  名称：

  Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production

  摘要：

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.

  DOI：

  10.1021/jm00142a024
• 作为产物：
  描述：

  (E)-3-thiophen-2-ylprop-2-enoyl azide 以 甲苯 为溶剂， 反应 1.0h， 生成 2-[(E)-2-isocyanatoethenyl]thiophene
  参考文献：
  名称：

  Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production

  摘要：

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.

  DOI：

  10.1021/jm00142a024

文献信息

• 5-Fluorouracil derivatives, preparation thereof and their pharmaceutical compositions
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0010941A1

  公开（公告）日：1980-05-14

  The present invention provides compounds of the general formula:- wherein R is an optionally substituted bridged alicyclic radical or a substituted lower alkyl radical, the substituent being an optionally substituted bridged alicyclic group, an amino, protected amino, lower alkoxy, acyl, lower alkylthio, cyano(lower)alkylthio, arylthio or optionally substituted heterocyclic radical or a carboxy and esterified carboxy group, with the proviso, that when the substituent is a carboxy or esterified carboxy group then the lower alkyl radical contains 3 to 6 carbon atoms; or an unsubstituted or substituted lower alkenyl radical, the substituent being an optionally substituted bridged alicyclic group, an optionally substituted aryl radical or an optionally substituted heterocyclic radical; or a halophenyl radical; or an optionally substituted heterocyclic radical. 'The present invention also provides processes for the preparation of these compounds and pharmaceutical composition containing them. Furthermore, the present invention is concerned with a method of treating cancer which comprises administering these compounds to mammals suffering from cancer.

  本发明提供通式为：- 的化合物。 其中 R 是任选取代的桥式脂环基或取代的低级烷基，取代基是任选取代的桥式脂环基、氨基、保护氨基、低级烷氧基、酰基、低级烷硫基、氰基（低级）烷硫基、芳硫基或任选取代的杂环基或羧基和酯化羧基，但条件是当取代基是羧基或酯化羧基时，低级烷基含有 3 至 6 个碳原子；或未取代或取代的低级烯基，取代基为任选取代的桥式脂环基、任选取代的芳基或任选取代的杂环基；或卤代苯基；或任选取代的杂环基。 '本发明还提供了制备这些化合物和含有这些化合物的药物组合物的工艺。此外，本发明还涉及一种治疗癌症的方法，该方法包括对患有癌症的哺乳动物施用这些化合物。
• US4349552A
  申请人：——

  公开号：US4349552A

  公开（公告）日：1982-09-14
• Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production
  作者：Robin D. Clark、Joan M. Caroon、Ian T. Harrison、Arthur F. Kluge、Stefan H. Unger、Howard R. Spires、Thomas R. Mathews

  DOI：10.1021/jm00142a024

  日期：1981.10

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.