N-(t-butyloxycarbonyl)-4-hydroxy-L-phenylalanine 4-pyridylamide | 109379-79-5

• 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: N-(t-butyloxycarbonyl)-4-hydroxy-L-phenylalanine 4-pyridylamide
• 英文别名: tert-butyl N-[(2S)-3-(4-hydroxyphenyl)-1-oxo-1-(pyridin-4-ylamino)propan-2-yl]carbamate
• CAS: 109379-79-5
• 化学式: C₁₉H₂₃N₃O₄
• 分子量: 357.409
• InChiKey: JZHDCUXTRWKUFS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二氯硝基苯 、 N-(t-butyloxycarbonyl)-4-hydroxy-L-phenylalanine 4-pyridylamide 以 二甲基亚砜 为溶剂， 生成 N-(t-butyloxycarbonyl)-4-(3-chloro-6-nitrophenoxy)-L-phenylalanine 4-pyridylamide dihydrochloride 、 N-(trans-4-aminomethylcyclohexylcarbonyl)-4-(3-chloro-6-nitrophenoxy)-L-phenylalanine 4-pyridylamide dihydrochloride
  参考文献：
  名称：

  Phenylalanine derivative and proteinase inhibitor

  摘要：

  一种具有以下式(I)的苯丙氨酸衍生物：##STR1##其中R.sup.1和R.sup.2独立地是氢，前提是R.sup.1和R.sup.2不同时是氢；C.sub.1-C.sub.8烷基，可以用羟基、羟基羰基、C.sub.1-C.sub.4烷氧羰基、C.sub.1-C.sub.4烷基硫醇基、C.sub.1-C.sub.4烷氧基、氨基甲酰基、磺胺基、吡啶基或苯基取代，这些基团可能进一步用硝基、C.sub.1-C.sub.4烷氧基或卤素取代；C.sub.6-C.sub.8环烷基，可以用羟基、C.sub.1-C.sub.4烷氧基、羟基羰基、C.sub.1-C.sub.4烷氧羰基或C.sub.1-C.sub.4烷基取代；苯基，可以用卤素、硝基、三氟甲基、C.sub.1-C.sub.4烷氧基、C.sub.1-C.sub.4烷基硫醇基、C.sub.1-C.sub.4烷基羰基、苯基羰基、羟基羰基、C.sub.1-C.sub.4烷氧羰基、氨基甲酰基、磺胺基、酰胺基、吡啶基羰基或C.sub.1-C.sub.6烷基取代，这些基团可能进一步用C.sub.1-C.sub.4烷基羰基、羟基羰基或C.sub.1-C.sub.4烷氧羰基取代；吡啶基，可以用卤素或C.sub.1-C.sub.4烷氧基取代；嘧啶基；N-苄基氮杂环己基；R.sup.1和R.sup.2可以与其连接的氮原子形成吗哪吗啉环结构；硫代吗哪吗啉；哌嗪基，可以用苯基羰基、苄基或C.sub.1-C.sub.4烷基取代；吡咯基，可以用羟基羰基或C.sub.1-C.sub.4烷氧羰基取代；以及哌啶基，可以用C.sub.1-C.sub.4烷基、苯基C.sub.1-C.sub.4烷基、苯基羰基或C.sub.1-C.sub.4烷氧羰基取代；X为氢、硝基、氨基或--OZ，其中Z为氢、C.sub.1-C.sub.4烷基、C.sub.2-C.sub.4烯基、苄基，可以用卤素、C.sub.1-C.sub.4烷基、硝基、三氟甲基、羟基羰基、C.sub.1-C.sub.4烷氧羰基或氰基取代；苯基羰基甲基；吡啶基甲基；苯基，可以用硝基或卤素取代；吡啶或嘧啶，可以用硝基取代；苯磺酰基，可以用C.sub.1-C.sub.4烷基取代；或苄氧羰基，可以用卤素取代；n为4至10；标记*表示碳的构型可以是D-构型、L-构型和DL-构型之一，或其药用可接受的盐。这种苯丙氨酸衍生物作为蛋白酶抑制剂具有有效性。

  公开号：

  US04895842A1

文献信息

• US4895842A
  申请人：——

  公开号：US4895842A

  公开（公告）日：1990-01-23
• Phenylalanine derivative and proteinase inhibitor
  申请人：Shosuke Okamoto

  公开号：US04895842A1

  公开（公告）日：1990-01-23

  A phenylalanine derivative having the formula (I): ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen provided that both R.sup.1 and R.sup.2 are not hydrogen at the same time; C.sub.1 -C.sub.8 alkyl which may be substituted with hydroxy, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkoxy, carbamoyl, sulfamoyl, pyridyl, or phenyl which may further be substituted with nitro, C.sub.1 -C.sub.4 alkoxy, or halogen; C.sub.6 -C.sub.8 cycloalkyl which may be substituted with hydroxy, C.sub.1 -C.sub.4 alkoxy, hydroxylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, or C.sub.1 -C.sub.4 alkyl; phenyl which may be substituted with halogen, nitro, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkylcarbonyl, phenylcarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, carbamoyl, sulfamoyl, amidino, pyridylcarbonyl, or C.sub.1 -C.sub.6 alkyl which may further be substituted with C.sub.1 -C.sub.4 alkylcarbonyl, hydroxycarbonyl, or C.sub.1 -C.sub.4 alkoxycarbonyl; pyridyl which may be substituted with halogen or C.sub.1 -C.sub.4 alkoxy; pyrimidyl; N-benzylazacyclohexyl; and R.sup.1 and R.sup.2 may form with the nitrogen atom attached thereto a ring structure as morpholino; thiomorpholino; piperazino which may be substituted with phenylcarbonyl, benzyl, or C.sub.1 -C.sub.4 alkyl; pyrrolidyl which may be substituted with hydroxycarbonyl or C.sub.1 -C.sub.4 alkoxycarbonyl; and piperidino substituted with C.sub.1 -C.sub.4 alkyl, phenyl C.sub.1 -C.sub.4 alkyl, phenycarbonyl, or C.sub.1 -C.sub.4 alkoxycarbonyl; X is hydrogen; nitro; amino; or --OZ wherein Z is hydrogen; C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.4 alkenyl; benzyl which may be substituted with halogen, C.sub.1 -C.sub.4 alkyl, nitro, trifluoromethyl, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, or cyano; phenylcarbonylmethyl; pyridylmethyl; phenyl which may be substituted with nitro or halogen; pyridyl or pyrimidyl which may be substituted with nitro; phenylsulfonyl which may be substituted with C.sub.1 -C.sub.4 alkyl; or benzyloxycarbonyl which may be substituted with halogen; n is 4 to 10; and the mark * indicates that the configuration of the carbon may be either one of D-configuration, L-configuration and DL-configuration or a pharmaceutical acceptable salt thereof. This phenylalanine derivative is effective as a proteinase inhibitor.

  一种具有以下式(I)的苯丙氨酸衍生物：##STR1##其中R.sup.1和R.sup.2独立地是氢，前提是R.sup.1和R.sup.2不同时是氢；C.sub.1-C.sub.8烷基，可以用羟基、羟基羰基、C.sub.1-C.sub.4烷氧羰基、C.sub.1-C.sub.4烷基硫醇基、C.sub.1-C.sub.4烷氧基、氨基甲酰基、磺胺基、吡啶基或苯基取代，这些基团可能进一步用硝基、C.sub.1-C.sub.4烷氧基或卤素取代；C.sub.6-C.sub.8环烷基，可以用羟基、C.sub.1-C.sub.4烷氧基、羟基羰基、C.sub.1-C.sub.4烷氧羰基或C.sub.1-C.sub.4烷基取代；苯基，可以用卤素、硝基、三氟甲基、C.sub.1-C.sub.4烷氧基、C.sub.1-C.sub.4烷基硫醇基、C.sub.1-C.sub.4烷基羰基、苯基羰基、羟基羰基、C.sub.1-C.sub.4烷氧羰基、氨基甲酰基、磺胺基、酰胺基、吡啶基羰基或C.sub.1-C.sub.6烷基取代，这些基团可能进一步用C.sub.1-C.sub.4烷基羰基、羟基羰基或C.sub.1-C.sub.4烷氧羰基取代；吡啶基，可以用卤素或C.sub.1-C.sub.4烷氧基取代；嘧啶基；N-苄基氮杂环己基；R.sup.1和R.sup.2可以与其连接的氮原子形成吗哪吗啉环结构；硫代吗哪吗啉；哌嗪基，可以用苯基羰基、苄基或C.sub.1-C.sub.4烷基取代；吡咯基，可以用羟基羰基或C.sub.1-C.sub.4烷氧羰基取代；以及哌啶基，可以用C.sub.1-C.sub.4烷基、苯基C.sub.1-C.sub.4烷基、苯基羰基或C.sub.1-C.sub.4烷氧羰基取代；X为氢、硝基、氨基或--OZ，其中Z为氢、C.sub.1-C.sub.4烷基、C.sub.2-C.sub.4烯基、苄基，可以用卤素、C.sub.1-C.sub.4烷基、硝基、三氟甲基、羟基羰基、C.sub.1-C.sub.4烷氧羰基或氰基取代；苯基羰基甲基；吡啶基甲基；苯基，可以用硝基或卤素取代；吡啶或嘧啶，可以用硝基取代；苯磺酰基，可以用C.sub.1-C.sub.4烷基取代；或苄氧羰基，可以用卤素取代；n为4至10；标记*表示碳的构型可以是D-构型、L-构型和DL-构型之一，或其药用可接受的盐。这种苯丙氨酸衍生物作为蛋白酶抑制剂具有有效性。