methyl 2-isocyanato-4-pentenoate | 128368-88-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-isocyanato-4-pentenoate
• 英文别名: methyl 2-isocyanatopent-4-enoate
• CAS: 128368-88-7
• 化学式: C₇H₉NO₃
• mdl: MFCD11041441
• 分子量: 155.153
• InChiKey: BIYPFLINERFAAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-isocyanato-4-pentenoate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 17.25h， 生成
  参考文献：
  名称：

  Structure-Based Design of Novel, Urea-Containing FKBP12 Inhibitors

  摘要：

  The structure-based design and subsequent chemical synthesis of novel, urea-containing FKBP12 inhibitors are described. These compounds are shown to disrupt the cis-trans peptidylprolyl isomerase activity of FKBP12 with inhibition constants (K-i,K-app) approaching 0.10 mu M. Analyses of several X-ray crystal structures of FKBP12-urea complexes demonstrate that the urea-containing inhibitors associate with FKBP12 in a manner that is similar to, but significantly different from, that observed for the natural product FK506.

  DOI：

  10.1021/jm950798a
• 作为产物：
  描述：

  DL-2-氨基-4-戊烯酸 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 methyl 2-isocyanato-4-pentenoate
  参考文献：
  名称：

  Structure-Based Design of Novel, Urea-Containing FKBP12 Inhibitors

  摘要：

  The structure-based design and subsequent chemical synthesis of novel, urea-containing FKBP12 inhibitors are described. These compounds are shown to disrupt the cis-trans peptidylprolyl isomerase activity of FKBP12 with inhibition constants (K-i,K-app) approaching 0.10 mu M. Analyses of several X-ray crystal structures of FKBP12-urea complexes demonstrate that the urea-containing inhibitors associate with FKBP12 in a manner that is similar to, but significantly different from, that observed for the natural product FK506.

  DOI：

  10.1021/jm950798a

文献信息

• Olefinic aryl oxime derivatives of hydantoins
  申请人：The Standard Oil Company

  公开号：US04868061A1

  公开（公告）日：1989-09-19

  This invention relates to new compounds of the formula: ##STR1## where each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 has zero to 10 C atoms, and no acetylenic unsaturation; each of R.sup.1, R.sup.2 and R.sup.3 is independently selected from H and hydrocarbyl; each of R.sup.4 and R.sup.5 is independently selected from H, hydrocarbyl and hydrocarbyl substituted with a group selected from: hydrocarbylcarbonylamino, di(hydrocarbylcarbonyl)amino, N-hydrocarbylcarbonyl(N-hydrocarbyl)amino, formylamino, diformylamino, and formyl(N-hydrocarbyl)amino, hydrocarbyloxy, hydrocarbylthio, formyl, formylthio, hydrocarbylcarbonyloxy, hydrocarbylcarbonylthio, hydrocarbyl carboxyl, hydrocarbyl thiocarboxyl, hydrocarbylamino, dihydrocarbylamino, hydrocarbylcarbonyl, 3-indolyl, 3-(1-hydrocarbyl)indolyl, 3-(1-hydrocarbylcarbonyl)indolyl, 3-(1-formyl)indolyl, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, 5-imidazolyl, 5-(3-hydrocarbyl)imidazolyl, 5-(3-hydrocarbylcarbonyl)imidazolyl, and 5-(3-formyl)imidazolyl, and where at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 contains olefinic unsaturation. The invention also relates to addition polymers of such compounds.

  这项发明涉及新化合物的公式：##STR1## 其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5中的每一个都具有0至10个碳原子，并且没有乙炔不饱和度；R.sup.1、R.sup.2和R.sup.3中的每一个都是独立选择自H和烃基；R.sup.4和R.sup.5中的每一个都是独立选择自H、烃基和烃基，烃基被选择自：烃基羰基氨基、二(烃基羰基)氨基、N-烃基羰基(N-烃基)氨基、甲酰氨基、二甲酰氨基和甲酰(N-烃基)氨基、烃氧基、烃硫基、甲酰基、甲酰硫基、烃基羰基氧基、烃基羰基硫基、烃基羧基、烃基硫羧基、烃基氨基、二烃基氨基、烃基羰基、3-吲哚基、3-(1-烃基)吲哚基、3-(1-烃基羰基)吲哚基、3-(1-甲酰)吲哚基、氨基甲酰基、烃基氨基甲酰基、二烃基氨基甲酰基、5-咪唑基、5-(3-烃基)咪唑基、5-(3-烃基羰基)咪唑基和5-(3-甲酰)咪唑基，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5中至少有一个含有烯丙基不饱和度。该发明还涉及这些化合物的加成聚合物。
• Olefinic N,N'-disubstituted ureas
  申请人：The Standard Oil Company

  公开号：US04977272A1

  公开（公告）日：1990-12-11

  This invention relates to new compounds of the formula: ##STR1## where each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 has zero to 10 C atoms, and no acetylenic unsaturation; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently selected from H and hydrocarbyl; with the proviso that R.sup.6 is C.sub.1 -C.sub.10 hydrocarbyl; each of R.sup.5 and R.sup.7 is independently selected from H, hydrocarbyl and hydrocarbyl substituted with a group selected from: hydrocarbylcarbonylamino, di(hydrocarbylcarbonyl)amino, N-hydrocarbylcarbonyl(N-hydrocarbyl)amino, formylamino, diformylamino, and formyl(N-hydrocarbyl)amino, hydrocarbyloxy, hydrocarbylthio, formyl, formylthio, hydrocarbylcarbonyloxy, hydrocarbylcarbonylthio, hydrocarbyl carboxyl, hydrocarbyl thiocarboxyl, hydrocarbylamino, dihydrocarbylamino, hydrocarbylcarbonyl, 3-indolyl, 3-(1-hydrocarbyl)indolyl, 3-(1-hydrocarbylcarbonyl)indolyl, 3-(1-formyl)indolyl, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, 5-imidazolyl, 5-(3-hydrocarbyl)imidazolyl, 5-(3-hydrocarbylcarbonyl)imidazolyl, and 5-(3-formyl)imidazolyl; and where at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 contains olefinic unsaturation. The invention also relates to addition polymers of such compounds.

  本发明涉及新的化合物的公式：##STR1## 其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6和R.sup.7每个都具有0到10个碳原子，并且没有乙炔不饱和度；R.sup.1、R.sup.2、R.sup.3和R.sup.4中的每一个都是独立选择自H和烃基；但R.sup.6是C.sub.1-C.sub.10烃基；R.sup.5和R.sup.7中的每一个都是独立选择自H、烃基和烃基取代的群，所选群从中选择：烃基羰基氨基、二(烃基羰基)氨基、N-烃基羰基(N-烃基)氨基、甲酰氨基、二甲酰氨基和甲酰(N-烃基)氨基，烃氧基、烃硫基、甲酰基、甲酰硫基、烃基羰基氧基、烃基羰基硫基、烃基羧基、烃基硫代羧基、烃基氨基、二烃基氨基、烃基羰基、3-吲哚基、3-(1-烃基)吲哚基、3-(1-烃基羰基)吲哚基、3-(1-甲酰)吲哚基、氨基甲酰、烃基氨基甲酰、二烃基氨基甲酰、5-咪唑基、5-(3-烃基)咪唑基、5-(3-烃基羰基)咪唑基和5-(3-甲酰)咪唑基；并且其中至少一个R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6和R.sup.7含有烯丙基不饱和度。本发明还涉及这种化合物的加成聚合物。
• US4868061A
  申请人：——

  公开号：US4868061A

  公开（公告）日：1989-09-19
• US4977272A
  申请人：——

  公开号：US4977272A

  公开（公告）日：1990-12-11
• Structure-Based Design of Novel, Urea-Containing FKBP12 Inhibitors
  作者：Peter S. Dragovich、John E. Barker、Judy French、Michael Imbacuan、Vincent J. Kalish、Charles R. Kissinger、Daniel R. Knighton、Cristina T. Lewis、Ellen W. Moomaw、Hans E. Parge、Laura A. K. Pelletier、Thomas J. Prins、Richard E. Showalter、John H. Tatlock、Kathleen D. Tucker、J. Ernest Villafranca

  DOI：10.1021/jm950798a

  日期：1996.1.1

  The structure-based design and subsequent chemical synthesis of novel, urea-containing FKBP12 inhibitors are described. These compounds are shown to disrupt the cis-trans peptidylprolyl isomerase activity of FKBP12 with inhibition constants (K-i,K-app) approaching 0.10 mu M. Analyses of several X-ray crystal structures of FKBP12-urea complexes demonstrate that the urea-containing inhibitors associate with FKBP12 in a manner that is similar to, but significantly different from, that observed for the natural product FK506.