cyclopentyl (S)-2-[(4-nitrobenzyl)amino]-4-methylpentanoate | 914382-80-2

• 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: cyclopentyl (S)-2-[(4-nitrobenzyl)amino]-4-methylpentanoate
• 英文别名: (S)-cyclopentyl 4-methyl-2-(4-nitrobenzylamino)pentanoate；cyclopentyl (2S)-4-methyl-2-[(4-nitrophenyl)methylamino]pentanoate
• CAS: 914382-80-2
• 化学式: C₁₈H₂₆N₂O₄
• 分子量: 334.415
• InChiKey: SAQXNPFYVLICLX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cyclopentyl (S)-2-[(4-nitrobenzyl)amino]-4-methylpentanoate 在 镍 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以61%的产率得到(S)-2-(4-amino-benzylamino)-4-methyl-pentanoic acid cyclopentyl ester
  参考文献：
  名称：

  WO2006/117567

  摘要：

  公开号：
• 作为产物：
  描述：

  cyclopentyl leucinate 、 对硝基溴化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 cyclopentyl (S)-2-[(4-nitrobenzyl)amino]-4-methylpentanoate
  参考文献：
  名称：

  WO2007/129040

  摘要：

  公开号：

文献信息

• DHFR Enzyme Inhibitors
  申请人：Davidson Alan Hornsby

  公开号：US20090118311A1

  公开（公告）日：2009-05-07

  Compounds of formula (I) or (II) are dihydrofolate reductase inhibitors, useful for the treatment of, for example, cell proliferative diseases: wherein A and D are independently —CHR 7 — or —NR 7 —; E and G are independently ═CR 7 — or ═N—; each R 6 independently represents hydrogen or —OR 7 ; R 7 is hydrogen or C 1 -C 6 alkyl; R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular carboxylesterase enzymes to a carboxylic acid group; R 2 is the side chain of a natural or non-natural alpha amino acid which does not contain a carboxyl, or carboxyl ester group; Y is a bond, —C(═O)—, —S(═O) 2 —, —C(═O)NR 3 —, —C(═S)—NR 3 , —C(═NH)NR 3 or —S(═O) 2 NR 3 — wherein R 3 is hydrogen or optionally substituted C 1 -C 6 alkyl; L 1 is a divalent radical of formula -(Alk 1 ) m (Q) n (Alk 2 ) p - wherein m, n and p are independently 0 or 1, and Q, Alk 1 and Alk 2 are as defined in the claims; X 1 represents a bond; —C(═O); or —S(═O) 2 —; —NR 4 C(═O)—, —C(═O)NR 4 —, —NR 4 C(═O)NR 5 —, —NR 4 S(═O) 2 —, or —S(═O) 2 NR 4 — wherein R 4 and R 5 are independently hydrogen or optionally substituted C 1 -C 6 alkyl; and z is 0 or 1.

  式(I)或(II)的化合物是二氢叶酸还原酶抑制剂，适用于治疗细胞增殖性疾病，其中A和D独立地为—CHR7—或—NR7—;E和G独立地为═CR7—或═N—;每个R6独立地表示氢或—OR7;R7是氢或C1-C6烷基;R1是羧酸基(—COOH)，或者是可由一个或多个细胞内羧酸酯酶水解为羧酸基的酯基;R2是天然或非天然α氨基酸的侧链，不含羧基或羧酯基;Y是键，—C(═O)—、—S(═O)2—、—C(═O)NR3—、—C(═S)—NR3、—C(═NH)NR3或—S(═O)2NR3—其中R3是氢或可选取代的C1-C6烷基;L1是式-(Alk1)m(Q)n(Alk2)p-的二价基团，其中m、n和p独立地为0或1，而Q、Alk1和Alk2如权利要求所定义;X1表示键;—C(═O);或—S(═O)2—;—NR4C(═O)—、—C(═O)NR4—、—NR4C(═O)NR5—、—NR4S(═O)2—或—S(═O)2NR4—其中R4和R5独立地为氢或可选取代的C1-C6烷基;z为0或1。
• P38 Map Kinase Inhibitors
  申请人：Moffat David Charles Festus

  公开号：US20090099185A1

  公开（公告）日：2009-04-16

  Compounds of formula (I) are inhibitors of p38 MAP kinase, and are therefore of utility in the treatment of, inter alia, inflammatory conditions including rheumatoid arthritis and COPD: wherein: G is —N═ or —CH═; D is an optionally substituted divalent mono- or bi-cyclic aryl or heteroaryl radical having 5-13 ring members; R 6 is hydrogen or optionally substituted C 1 -C 3 alkyl; P represents hydrogen and U represents a radical of formula (IA); or U represents hydrogen and P represents a radical of formula -A-(CH 2 ), —X 1 -L 1 -Y—NH—CHR 1 R 2 wherein A represents an optionally substituted divalent mono- or bicyclic carbocyclic or heterocyclic radical having 5-13 ring members; z, Y, L 1 , and X 1 are as defined in the specification; R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular esterase enzymes to a carboxylic acid group; and R 2 is the side chain of a natural or non-natural alpha amino acid.

  式(I)的化合物是p38 MAP激酶的抑制剂，因此在治疗炎症性疾病，包括类风湿性关节炎和COPD方面有用。其中：G是—N═或—CH═；D是一个可选取代的二价单环或双环芳基或杂环基，具有5-13个环成员；R6是氢或可选取代的C1-C3烷基；P代表氢，U代表公式(IA)的基团；或U代表氢，P代表公式-A-(CH2)-、—X1-L1-Y—NH—CHR1R2的基团，其中A代表可选取代的二价单环或双环碳环或杂环基，具有5-13个环成员；z、Y、L1和X1如规范中所定义；R1是羧酸基(—COOH)，或可由一个或多个细胞内酯酶酶水解为羧酸基的酯基；R2是天然或非天然α氨基酸的侧链。
• DHFR enzyme inhibitors
  申请人：Chroma Therapeutics Ltd.

  公开号：US08211900B2

  公开（公告）日：2012-07-03

  Compounds of formula (I) or (II) are dihydrofolate reductase inhibitors, useful for the treatment of, for example, cell proliferative diseases: wherein A and D are independently —CHR7— or —NR7—; E and G are independently ═CR7— or ═N—; each R6 independently represents hydrogen or —OR7; R7 is hydrogen or C1-C6 alkyl; R1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular carboxylesterase enzymes to a carboxylic acid group; R2 is the side chain of a natural or non-natural alpha amino acid which does not contain a carboxyl, or carboxyl ester group; Y is a bond, —C(═O)—, —S(═O)2—, —C(═O)NR3—, —C(═S)—NR3, —C(═NH)NR3 or —S(═O)2NR3— wherein R3 is hydrogen or optionally substituted C1-C6 alkyl; L1 is a divalent radical of formula -(Alk1)m(Q)n(Alk2)p- wherein m, n and p are independently 0 or 1, and Q, Alk1 and Alk2 are as defined in the claims; X1 represents a bond; —C(═O); or —S(═O)2—; —NR4C(═O)—, —C(═O)NR4—, —NR4C(═O)NR5—, —NR4S(═O)2—, or —S(═O)2NR4— wherein R4 and R5 are independently hydrogen or optionally substituted C1-C6 alkyl; and z is 0 or 1.

  式(I)或(II)的化合物是二氢叶酸还原酶抑制剂，可用于治疗细胞增殖性疾病，其中A和D独立地为-CHR7-或-NR7-; E和G独立地为═CR7-或═N-; 每个R6独立地表示氢或-OR7; R7为氢或C1-C6烷基; R1为羧酸基(—COOH)或可由一个或多个细胞内羧酸酯酶水解为羧酸基的酯基; R2为天然或非天然α氨基酸的侧链，不含羧基或羧酯基; Y为键，-C(═O)-，-S(═O)2-，-C(═O)NR3-，-C(═S)-NR3，-C(═NH)NR3或-S(═O)2NR3-，其中R3为氢或可选取代的C1-C6烷基; L1为式-(Alk1)m(Q)n(Alk2)p-的二价基团，其中m、n和p独立地为0或1，Q、Alk1和Alk2如权利要求所定义; X1表示键，-C(═O); 或-S(═O)2-; -NR4C(═O)-，-C(═O)NR4-，-NR4C(═O)NR5-，-NR4S(═O)2-或-S(═O)2NR4-，其中R4和R5独立地为氢或可选取代的C1-C6烷基; z为0或1。
• ENZYME AND RECEPTOR MODULATION
  申请人：Chroma Therapeutics Ltd

  公开号：US20150126534A1

  公开（公告）日：2015-05-07

  Covalent conjugation of an alpha amino acid ester to a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid, leads to accumulation of the carboxylic acid hydrolysis product in the cell and enables improved or more prolonged enzyme or receptor modulation relative to the unconjugated modulator.

  将α-氨基酸酯共价连接到靶向细胞内酶或受体活性调节剂上，其中共轭物的酯基可被一个或多个细胞内羧酸酯酶水解为相应的酸，导致羧酸水解产物在细胞内积累，并相对于未共轭的调节剂实现改善或更长时间的酶或受体调节。
• Enzyme and Receptor Modulation
  申请人：Davidson Alan Hornsby

  公开号：US20090215800A1

  公开（公告）日：2009-08-27

  Covalent conjugation of an alpha amino acid ester to a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid, leads to accumulation of the carboxylic acid hydrolysis product in the cell and enables improved or more prolonged enzyme or receptor modulation relative to the unconjugated modulator.

  将α-氨基酸酯与靶向细胞内酶或受体活性的调节剂共价结合，其中共轭物的酯基可被一个或多个细胞内羧酸酯酶水解为相应的酸，导致羧酸水解产物在细胞内积累，并使相对于未共轭的调节剂，酶或受体的调节改善或更长久。