3,4-Diacetoxy-L-phenylalanin-benzylester | 63236-47-5

• 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: 3,4-Diacetoxy-L-phenylalanin-benzylester
• 英文别名: 3,4-diacetyloxy-L-phenylalanine benzyl ester；3,4-diacetyloxy-L-phenylalanine-benzyl ester；benzyl (2S)-2-amino-3-(3,4-diacetyloxyphenyl)propanoate
• CAS: 63236-47-5
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: QGSHZMFEVDSXGR-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-Diacetoxy-L-phenylalanin-benzylester 以 三乙胺 为溶剂， 以For instance, 3,4-dihydroxy-L-phenylalanine-benzyl ester was obtained quantitatively if a large excess of triethylamine的产率得到3,4-二羟基-L-苯丙氨酸苄基酯
  参考文献：
  名称：

  Novel, transient pro-drug forms of L-DOPA

  摘要：

  提供了新型的、短暂的L-DOPA（3,4-二羟基-L-苯丙氨酸）前药形式，其化学式为：##STR1## 其中n表示相对于公式（V-A）的整数为2到50，n表示相对于公式（V-B）的整数为1到50；R表示氢原子、酰基、##STR2## --CO-吡啶基或--CO--R.sub.3，其中R.sub.3是任何N,N-C.sub.1-C.sub.2二烷基氨基酸或C.sub.4-C.sub.6环烷基氨基酸的残基；R.sub.1表示--OH、--O-低碳基、--O-苯甲基或自然存在的蛋白质氨基酸；R.sub.2表示##STR3## --CO-吡啶基、自然存在的蛋白质氨基酸、3',4'-L-二酰基氧基苯丙氨酸或--CO-R.sub.3。这些化合物在帕金森病的治疗中都是有用的。

  公开号：

  US03998799A1

文献信息

• Novel, transient pro-drug forms of l-dopa useful in the treatment of
  申请人：Interx Research Corporation

  公开号：US03939253A1

  公开（公告）日：1976-02-17

  There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##SPC1## Wherein R represents a member selected from the group consisting of a hydrogen atom, a --COCH.sub.3 group, a --COC.sub.2 H.sub.5 group, a --COOC.sub.2 H.sub.5 group, and a --CO--C(CH.sub.3).sub.3 group; wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group, a --OM group (wherein M represents an alkali metal or an ammonium ion), a --OCH.sub.2 --C.sub.6 H.sub.5 group, a --OCH.sub.3 group, a --OC.sub.2 H.sub.5 group, and --NH--CH(R.sub.3)COOH group, wherein R.sub.3 represents the residue of any naturally occurring amino acid; and wherein R.sub.2 represents a member selected from the group consisting of a hydrogen atom, a formyl group, a --CO--C.sub.6 H.sub.5 group, a --CO--pyridyl group, a --CO(R.sub.5)--CH=CH(R.sub.4) group, and a NH.sub.2 --CH(R.sub.6)--CO-- group, wherein R.sub.4 represents a methyl group and wherein R.sub.5 represents a member selected from the group consisting of a methyl group, a --OC.sub.2 H.sub.5 group, and a C.sub.6 H.sub.5 -- group, and wherein R.sub.6 represents the residue of any naturally occurring amino acid, With the proviso that simultaneously, R cannot represent a hydrogen atom when R.sub.1 represents a --OCH.sub.3 group or a --OH group and when R.sub.2 represents a hydrogen atom respectively; R cannot represent a hydrogen atom when R.sub.1 represents either a hydroxyl group or a --OCH.sub.3 group and R.sub.2 represents a --COCH.sub.3 group, respectively; R cannot represent a hydrogen atom when R.sub.1 represents a hydroxyl group and R.sub.2 represents a formyl group respectively, R cannot represent a hydrogen atom when R.sub.1 represents a hydroxyl group and R.sub.2 represents a benzoyl group, respectively; and, R cannot represent a hydrogen atom when R.sub.1 represents a hydroxyl group and R.sub.6 represents the residue of L-leucine, respectively. These compounds are useful in the treatment of Parkinson's Disease.

  提供了新颖的、临时的L-DOPA（3,4-二羟基-L-苯丙氨酸）前药形式，其化学式为：##SPC1## 其中R表示从羟基原子、--COCH.sub.3基团、--COC.sub.2 H.sub.5基团、--COOC.sub.2 H.sub.5基团和--CO--C(CH.sub.3).sub.3基团中选择的一种成员；其中R.sub.1表示从羟基基团、--OM基团（其中M表示碱金属或铵离子）、--OCH.sub.2--C.sub.6 H.sub.5基团、--OCH.sub.3基团、--OC.sub.2 H.sub.5基团和--NH--CH(R.sub.3)COOH基团中选择的一种成员，其中R.sub.3表示任何天然氨基酸的残基；其中R.sub.2表示从氢原子、甲酰基团、--CO--C.sub.6 H.sub.5基团、--CO--吡啶基团、--CO(R.sub.5)--CH=CH(R.sub.4)基团和NH.sub.2--CH(R.sub.6)--CO--基团中选择的一种成员，其中R.sub.4表示甲基基团，R.sub.5表示从甲基基团、--OC.sub.2 H.sub.5基团和C.sub.6 H.sub.5--基团中选择的一种成员，R.sub.6表示任何天然氨基酸的残基，但同时，当R.sub.1分别表示--OCH.sub.3基团或--OH基团且R.sub.2分别表示氢原子时，R不能表示氢原子；当R.sub.1分别表示羟基或--OCH.sub.3基团且R.sub.2分别表示--COCH.sub.3基团时，R不能表示氢原子；当R.sub.1表示羟基且R.sub.2表示甲酰基团时，R不能表示氢原子；当R.sub.1表示羟基且R.sub.2表示苯甲酰基团时，R不能表示氢原子；当R.sub.1表示羟基且R.sub.6表示L-亮氨酸的残基时，R不能表示氢原子。这些化合物在帕金森病的治疗中是有用的。
• Novel, transient pro-drug forms of L-DOPA to treat Parkinson's disease
  申请人：Interx Research Corporation

  公开号：US04035507A1

  公开（公告）日：1977-07-12

  There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##STR1## wherein R represents a hydrogen atom, an acyl group, ##STR2## group, a -CO-pyridyl group, and a -CO-R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-C.sub.1 -C.sub.2 dialkylamino acid or a C.sub.4 -C.sub.6 cycloalkylamino acid (e.g., ##STR3## wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group and a --OM group, wherein M is an alkali metal (Na, K, etc.) or an ammonium ion; and wherein R.sub.2 represents a member selected from the group consisting of a ##STR4## group, a -CO-pyridyl group, and a --CO-R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-(C.sub.1 -C.sub.2)--dialkylamino acid or a C.sub.4 -C.sub.6 -cycloalkylamino acid (e.g., ##STR5## wherein R represents an acyl group; wherein R.sub.2 represents a hydrogen atom; and wherein R.sub.1 represents a --NHCH(R.sub.4)COOR.sub.5 group, wherein R.sub.4 represents the residue of any naturally occurring amino acid, and wherein R.sub.5 represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group (e.g., methyl, ethyl, propyl, butyl, pentyl), and a C.sub.1 -C.sub.5 alkylaryl group (e.g., --CH.sub.2 -C.sub.6 H.sub.5, --CH.sub.2 -CH.sub.2 --C.sub.6 H.sub.5, etc.), and the HX salts thereof, wherein X is a conventional pharmaceutically acceptable acid addition salt anion (e.g., chloride, bromide, perchlorate, methanesulfonate, succinate, etc.); ##STR6## wherein R represents an acyl group; wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group, a --OCH.sub.3 group, a --OC.sub.2 H.sub.5 group, a --OC.sub.3 H.sub.7 group, a --OC.sub.4 H.sub.9 group, and a -OCH.sub.2 -C.sub.6 H.sub.5 group; and wherein R.sub.2 represents an NH.sub.2 CH(R.sub.6)CO-- group, wherein R.sub.6 represents the residue of any naturally occurring amino acid, and the HX salts thereof, wherein X is defined as above; ##STR7## wherein R represents a member selected from the group consisting of an acyl group; wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group, a --OCH.sub.3 group, a --OC.sub.2 H.sub.5 group, a --OC.sub.3 H.sub.7 group, a --OC.sub.4 H.sub.9 group, and a --OCH.sub.2 -C.sub.6 H.sub.5 group; and wherein R.sub.2 represents an NH.sub.2 -CH(R.sub.7)--CO-- group, wherein R.sub.7 represents the residue of a 3,4-L-diacylphenylalanine group having the formula: ##STR8## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR9## wherein n represents an integer of from 2 to 50 with respect to formula (V-A), and wherein n represents an integer of from 1 to 50 with respect to formula (V-B). These compounds are all useful in the treatment of Parkinson's Disease.

  提供了L-DOPA（3,4-二羟基-L-苯丙氨酸）的新型临时前药形式，其化学式为：##STR1## 其中R表示氢原子，酰基，##STR2##基，-CO-吡啶基团和-CO-R.sub.3基团，其中R.sub.3表示任何N，N-C.sub.1-C.sub.2二烷基氨基酸或C.sub.4-C.sub.6环烷基氨基酸的残基（例如，##STR3##其中R.sub.1表示从羟基和--OM基组成的群中选择的一种成员，其中M是碱金属（Na，K等）或铵离子；R.sub.2表示从##STR4##基团，-CO-吡啶基团和--CO-R.sub.3基团中选择的一种成员，其中R.sub.3表示任何N，N-（C.sub.1-C.sub.2）-二烷基氨基酸或C.sub.4-C.sub.6-环烷基氨基酸的残基（例如，##STR5##其中R表示酰基；R.sub.2表示氢原子；R.sub.1表示--NHCH（R.sub.4）COOR.sub.5基团，其中R.sub.4表示任何天然氨基酸的残基，R.sub.5表示从氢原子，C.sub.1-C.sub.5烷基（例如，甲基，乙基，丙基，丁基，戊基）和C.sub.1-C.sub.5烷基芳基（例如，--CH.sub.2-C.sub.6H.sub.5，--CH.sub.2-CH.sub.2--C.sub.6H.sub.5等）中选择的一种成员，以及其HX盐，其中X是传统的药用可接受酸盐阴离子（例如，氯化物，溴化物，高氯酸盐，甲磺酸盐，琥珀酸盐等）；##STR6##其中R表示酰基；R.sub.1表示从羟基，--OCH.sub.3基，--OC.sub.2H.sub.5基，--OC.sub.3H.sub.7基，--OC.sub.4H.sub.9基和--OCH.sub.2-C.sub.6H.sub.5基中选择的一种成员；R.sub.2表示NH.sub.2CH（R.sub.6）CO--基团，其中R.sub.6表示任何天然氨基酸的残基，以及其HX盐，其中X如上所述；##STR7##其中R表示从酰基中选择的一种成员；R.sub.1表示从羟基，--OCH.sub.3基，--OC.sub.2H.sub.5基，--OC.sub.3H.sub.7基，--OC.sub.4H.sub.9基和--OCH.sub.2-C.sub.6H.sub.5基中选择的一种成员；R.sub.2表示NH.sub.2-CH（R.sub.7）--CO--基团，其中R.sub.7表示具有以下式子的3,4-L-二酰基苯丙氨酸基团的残基：##STR8##其中R如上所述，以及其HX盐，其中X如上所述；和##STR9##其中n表示相对于式（V-A）的整数为2至50，相对于式（V-B）的整数为1至50。这些化合物在帕金森病的治疗中都有用。
• N-Nicotinoyl-3,4-dinicotinoyloxy-L-phenylalanine and derivatives
  申请人：INTERx Research Corporation

  公开号：US04065566A1

  公开（公告）日：1977-12-27

  There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##STR1## wherein R represents a hydrogen atom, an acyl group, a ##STR2## group, a --CO-pyridyl group, and a --CO--R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-C.sub.1 -C.sub.2 dialkylamino acid or a C.sub.4 -C.sub.6 cycloalkylamino acid ##STR3## wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group and a --OM group, wherein M is an alkali metal (Na, K, etc.) or an ammonium ion; and wherein R.sub.2 represents a member selected from the group consisting of a ##STR4## group, a --CO-pyridyl group, and a --CO--R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-(C.sub.1 -C.sub.2)-dialkylamino acid or a C.sub.4 -C.sub.6 -cycloalkylamino acid ##STR5## wherein R represents an acyl group; wherein R.sub.2 represents a hydrogen atom; and wherein R.sub.1 represents a --NHCH(R.sub.4)COOR.sub.5 group, wherein R.sub.4 represents the residue of any naturally occurring amino acid, and wherein R.sub.5 represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group (e.g., methyl, ethyl, propyl, butyl, pentyl), and a C.sub.1 -C.sub.5 alkylaryl group (e.g., --CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --CH.sub.2 --C.sub.6 H.sub.5, etc.), and the HX salts thereof, wherein X is a conventional pharmaceutically acceptable acid addition salt anion (e.g. chloride, bromide, perchlorate, methanesulfonate, succinate, etc.). These compounds are all useful in the treatment of Parkinson's Disease.

  提供了新型的、短暂的L-DOPA（3,4-二羟基-L-苯丙氨酸）的前药形式，其化学式为：##STR1## 其中R代表氢原子、酰基、##STR2##基团、--CO-吡啶基团和--CO--R.sub.3基团，其中R.sub.3代表任何N,N-C.sub.1-C.sub.2二烷基氨基酸或C.sub.4-C.sub.6环烷基氨基酸的残基##STR3## 其中R.sub.1代表羟基和--OM基团中的一员，其中M是碱金属（Na、K等）或铵离子；R.sub.2代表##STR4##基团、--CO-吡啶基团和--CO--R.sub.3基团中的一员，其中R.sub.3代表任何N,N-(C.sub.1-C.sub.2)-二烷基氨基酸或C.sub.4-C.sub.6-环烷基氨基酸的残基##STR5## 其中R代表酰基；R.sub.2代表氢原子；R.sub.1代表--NHCH(R.sub.4)COOR.sub.5基团，其中R.sub.4代表任何天然氨基酸的残基，R.sub.5代表羟基、C.sub.1-C.sub.5烷基（例如，甲基、乙基、丙基、丁基、戊基）和C.sub.1-C.sub.5烷基芳基基团（例如，--CH.sub.2--C.sub.6 H.sub.5，--CH.sub.2--CH.sub.2--C.sub.6 H.sub.5等），以及其HX盐，其中X是常规的药用可接受的酸盐阴离子（例如氯化物、溴化物、高氯酸盐、甲磺酸盐、琥珀酸盐等）。这些化合物都可用于治疗帕金森病。
• AMINO ACID DERIVATIVES
  申请人：Proximagen Ltd.

  公开号：EP1981901A1

  公开（公告）日：2008-10-22
• Amino Acid Derivatives
  申请人：Hobbs Christopher

  公开号：US20090170937A1

  公开（公告）日：2009-07-02

  Compounds of formula (I) have activity in alleviating the effects of impaired dopaminergic signaling, for example in the treatment of Parkinsons Disease: wherein: R 1 is a carboxyl, carboxyl ester, or carboxamide group; R 2 and R 3 are independently hydrogen, or a group —C(═O)R 6 or —C(═O)OR 6 wherein Re is C 1 -C 6 alkyl, or a group —CH 2 Q wherein Q is an optionally substituted monocyclic carbocyclic or heterocyclyl ring of 3 to 6 ring atoms; R 4 and R 5 are independently (a) the side chain of a natural amino acid, or (b) optionally substituted C 1 -C 4 alkyl, C 2 -C 4 alkenyl, or C 2 -C 4 alkynyl, or (c) —CH 2 XCH 3 , —CH 2 CH 2 XCH 3 , or —CH 2 XCH 2 CH 3 , wherein X is —O—, S, or —NR 7 wherein R 7 is hydrogen, methyl or ethyl; or (d) —CH 2 Q or CH 2 OQ wherein Q is as defined in relation to R 6 ; or R 4 and R 5 taken together with the carbon atom to which they are attached form an optionally substituted cycloalkyl or heterocyclic ring of 3 to 8 ring atoms, optionally fused to a second, optionally substituted, carbocyclic or heterocyclic ring