(S)-3-(2-(tert-butoxycarbonylamino)propanamido)propanoic acid | 67818-91-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-3-(2-(tert-butoxycarbonylamino)propanamido)propanoic acid
• 英文别名: 3-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid
• CAS: 67818-91-1
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: QJJCUPDRDSRYAH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(2-(tert-butoxycarbonylamino)propanamido)propanoic acid 在 甲酸 、 四丁基氟化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 64.0h， 生成
  参考文献：
  名称：

  Synthesis and activity of 5′-Uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A

  摘要：

  A series of 5'-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-beta-alanyl- and aminoacyl-N-methyl-beta-alanyl- dipeptides were attached either via an ester linkage to the 5'-hydroxyl of uridine. or via an amide linkage to 5-amino-5-deoxyuridine. The most active inhibitor of Escherichia coli phosphoMurNAc-pentapeptide translocase (MraY) was 5'-O-((L)-Ala-N-methyl-beta-alanyl)-uridine (131), which also showed 97% enzyme inhibition at 2.35mM concentration, and showed antibacterial activity at 100 mug/mL concentration against Pseudomonas putida. Both the central N-methyl amide linkage and a 5' uridine ester linkage were required for highest biological activity. Enzyme inhibition was shown to be competitive with Mg2+. It is proposed that the primary amino terminus of the inhibitor binds in place of the Mg2+. cofactor at the MraY active site, positioned via a cis-N-methyl amide linkage. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00270-0
• 作为产物：
  描述：

  (2S)-methyl N-(Boc)alaninyl-β-alaninate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以75%的产率得到(S)-3-(2-(tert-butoxycarbonylamino)propanamido)propanoic acid
  参考文献：
  名称：

  Synthesis and activity of 5′-Uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A

  摘要：

  A series of 5'-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-beta-alanyl- and aminoacyl-N-methyl-beta-alanyl- dipeptides were attached either via an ester linkage to the 5'-hydroxyl of uridine. or via an amide linkage to 5-amino-5-deoxyuridine. The most active inhibitor of Escherichia coli phosphoMurNAc-pentapeptide translocase (MraY) was 5'-O-((L)-Ala-N-methyl-beta-alanyl)-uridine (131), which also showed 97% enzyme inhibition at 2.35mM concentration, and showed antibacterial activity at 100 mug/mL concentration against Pseudomonas putida. Both the central N-methyl amide linkage and a 5' uridine ester linkage were required for highest biological activity. Enzyme inhibition was shown to be competitive with Mg2+. It is proposed that the primary amino terminus of the inhibitor binds in place of the Mg2+. cofactor at the MraY active site, positioned via a cis-N-methyl amide linkage. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00270-0

文献信息

• Prodrugs of Compounds that Enhance Antifungal Activity and Compositions of Said Prodrugs
  申请人：MethylGene Inc.

  公开号：US20150203517A1

  公开（公告）日：2015-07-23

  The invention relates to prodrugs for use in the inhibition of histone deacetylase. The prodrugs of the present invention have good aqueous solubility and good aqueous stability. The prodrugs of the invention advantageously are metabolized to the active ingredient in plasma or in the blood stream of a warm-blooded animal. The invention also provides compositions and, and methods for making the prodrugs, and methods for using the prodrugs to treat fungal infections.

  该发明涉及用于抑制组蛋白去乙酰化酶的前药。本发明的前药具有良好的水溶性和良好的水稳定性。本发明的前药有利地在温血动物的血浆或血液中代谢成活性成分。该发明还提供了制备前药的组合物和方法，以及使用前药治疗真菌感染的方法。
• Prodrugs of excitatory amino acids
  申请人：ELI LILLY AND COMPANY

  公开号：EP1310482A1

  公开（公告）日：2003-05-14

  This invention relates to synthetic excitatory amino acid prodrugs of the formula I wherein R11 is CO2R14 and R12 is hydrogen or fluoro; or R11 is hydrogen or fluoro and R12 is CO2R14; R13 and R14 are, independently, hydrogen, (1-10C) alkyl, (2-4C) alkenyl, aryl or arylalkyl; A is (Q)p-; p is any integer from 1-10; and Q is independently selected, each time taken, from the group amino acyl; provided that the compound is not one on which R11 is CO2R14; R12, R13 and R14 are hydrogen; p is 1; and Q is L-alanyl; or a pharmaceutically acceptable salt thereof and processes for their preparation. The invention further relates to methods of using, and pharmaceutical composition comprising, the compounds for the treatment of neurological disorders and psychiatric disorders.

  本发明涉及公式I的合成兴奋性氨基酸前药，其中R11为CO2R14且R12为氢或氟；或R11为氢或氟且R12为CO2R14；R13和R14分别为氢、(1-10C)烷基、(2-4C)烯基、芳基或芳基烷基；A为(Q)p-；p为1-10的任意整数；Q每次从氨基酰基组中独立选择；前提是该化合物不是R11为CO2R14；R12、R13和R14为氢；p为1；Q为L-丙氨酰；或其药学上可接受的盐及其制备方法。本发明还涉及使用这些化合物以及包含这些化合物的药物组合物治疗神经疾病和精神疾病的方法。
• [EN] PRODRUGS OF EXCITATORY AMINO ACIDS<br/>[FR] PROMEDICAMENTS D'ACIDES AMINES EXCITATEURS
  申请人：LILLY CO ELI

  公开号：WO2002055485A1

  公开（公告）日：2002-07-18

  This invention relates to synthetic excitatory amino acid prodrugs of formula (I), wherein R11 is CO¿2?R?14 and R12¿ is hydrogen or fluoro; or R11 is hydrogen or fluoro and R12 is CO¿2?R?14; R13 and R14¿ are, independently, hydrogen, (1-10C) alkyl, (2-4C) alkenyl, aryl or arylalkyl; A is (Q)p; p is an integer from 1-10; and Q is independently selected, each time taken, from the group amino acyl; provided that the compound is not one in which R11 is CO¿2?R?14; R12, R13 and R14¿ are hydrogen; p is any integer from 1-10; and Q is independently selected, each time taken, from the group amino acyl; provided that the compound is not one in which R11 is CO¿2?R?14; R12, R13 and R14¿ are hydrogen; p is 1; and Q is L-alanyl; or a pharmaceutically acceptable salt thereof and processes for their preparation. The invention further relates to methods of using, and pharmaceutical compositions comprising, the compounds for the treatment of neurological disorders and psychiatric disorders.

  本发明涉及式(I)的合成兴奋性氨基酸前药，其中R11为CO2R14，R12为氢或氟；或R11为氢或氟，R12为CO2R14；R13和R14独立地为氢，(1-10C)烷基，(2-4C)烯基，芳基或芳基烷基；A为(Q)p；p为1-10的整数；Q每次均从氨基酰基组中独立选择；但化合物不是其中R11为CO2R14，R12，R13和R14为氢，p为1-10的任何整数，Q每次从氨基酰基组中独立选择；但化合物不是其中R11为CO2R14，R12，R13和R14为氢，p为1，Q为L-丙氨酰基；或其药学上可接受的盐及其制备方法。本发明还涉及使用该化合物和制药组合物治疗神经系统和精神系统疾病的方法。
• Phosphonate and phosphonamide endopeptidase inhibitors
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0306879A2

  公开（公告）日：1989-03-15

  Compounds of the formula wherein Y is O or NH and X is will inhibit the action of neutral endopeptidase. As a result, such compounds produce diuresis, natriuresis, and lower blood pressure as well as relieving pain when administered to a mammalian host.

  式中的化合物 其中 Y 为 O 或 NH，X 为 将抑制中性内肽酶的作用。因此，当哺乳动物宿主服用此类化合物时，可产生利尿、利尿、降低血压以及缓解疼痛的作用。
• PRODRUGS OF EXCITATORY AMINO ACIDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1351925A1

  公开（公告）日：2003-10-15