(S)-2-amino-N-isopentylpropanamide hydrochloride | 72155-60-3

• 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: (S)-2-amino-N-isopentylpropanamide hydrochloride
• 英文别名: L-Ala-NHⁱC5H11*HCl；Ala-Iaa hydrochloride；(2S)-2-amino-N-(3-methylbutyl)propanamide;hydrochloride
• CAS: 72155-60-3
• 化学式: C₈H₁₈N₂O*ClH
• 分子量: 194.705
• InChiKey: ABUVTRMWDPZJGW-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-isopentylpropanamide hydrochloride 在 盐酸 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 Acetic acid (S)-2-((S)-2-amino-3-methyl-butyrylamino)-4-methyl-1-{2-[(S)-1-(3-methyl-butylcarbamoyl)-ethylcarbamoyl]-ethyl}-pentyl ester
  参考文献：
  名称：

  Holladay, Mark W.; Salituro, Francesco G.; Rich, Daniel H., Journal of Medicinal Chemistry, 1987, vol. 30, p. 375 - 383

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氨基-3-甲基丁烷 盐酸盐 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-2-amino-N-isopentylpropanamide hydrochloride
  参考文献：
  名称：

  Additivity or cooperativity: Which model can predict the influence of simultaneous incorporation of two or more functionalities in a ligand molecule?

  摘要：

  Predicting how binding affinity responds to ligand structural modifications in structure-activity relationship studies (SAR) is a major challenge in medicinal chemistry. This is particularly true when two or more of these modifications are carried out simultaneously. In this study, we present binding affinity data from several series of thermolysin inhibitors in which simultaneous structural modifications were investigated to determine whether they are cooperative or additive. Data revealed that, while additivity is at work in some cases, cooperativity is more commonly demonstrated. Cooperativity and additivity were then correlated with ligand descriptors, such as the spacing and the topological features of the modified groups, in a manner that may provide guidance as to when each model should be utilized. Cooperativity was particularly associated with contiguous groups and small unbranched hydrophobic side chain. Additivity, on the other hand, was associated with moderately distant hydrophobic group combinations and side chain branching. Such correlations can improve the predictability of SAR studies and can provide a starting point for additional investigations that may lead to further significant enhancements in the current scoring functions. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.056

文献信息

• Synthesis of analogs of the carboxyl protease inhibitor pepstatin. Effect of structure on inhibition of pepsin and renin
  作者：Daniel H. Rich、Eric T. O. Sun、Edgar Ulm

  DOI：10.1021/jm00175a006

  日期：1980.1

  Analogues of the carboxyl protease inhibitor, pepstatin, were synthesized from optically pure forms of N-(tert-butoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid (Boc-Sta), and the inhibition of pepsin and renin was determined. In addition, the new amino acid (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid [AHPPA] was synthesized and the stereochemistry of the 3 and 4 positions established.

  由光学纯的N-（叔丁氧羰基）-4-氨基-3-羟基-6-甲基庚酸（Boc-Sta）合成羧基蛋白酶抑制剂胃蛋白酶抑制素的类似物，胃蛋白酶和肾素的抑制作用为决心。另外，合成了新的氨基酸（3S，4S）-4-氨基-3-羟基-5-苯基戊酸[AHPPA]，并建立了3和4位的立体化学。三肽异戊酰基-L-戊酰基-（3S，4S）-4-氨基-3-羟基-6-甲基庚酰基-L-丙氨酸异戊酰胺[Iva-Val-（3S，4S）-Sta-Ala-NHiC5H11]和Iva-发现Val-（3S，4S）-AHPPA-Ala-NHiC5H11是胃蛋白酶的有效抑制剂，Ki分别为1 x 10（-9）和0.9 x 10（-9）M。将（3S）-羟基的手性更改为3R或缩短肽链可减少与胃蛋白酶的结合力100倍以上。
• Novel peptidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0195212A2

  公开（公告）日：1986-09-24

  This invention relates to analogs of peptidase substrates in which the amide group containing the scissile amide bond of the substrate peptide has been replaced by an activated electrophilic ketone moiety. These analogs of the peptidase substrates provide specific enzyme inhibitors for a variety of proteases, the inhibition of which will have useful physiological consequences in a variety of disease states.

  本发明涉及肽酶底物的类似物，在这些类似物中，含有底物肽的巯基酰胺键的酰胺基团已被活化的亲电酮分子取代。这些肽酶底物类似物为多种蛋白酶提供了特异性酶抑制剂，其抑制作用将对多种疾病产生有益的生理影响。
• Synthesis of novel 3-methylstatine analogs. Assignment of absolute configuration
  作者：Megumi Kawai、Amrit S. Boparai、Michael S. Bernatowicz、Daniel H. Rich

  DOI：10.1021/jo00159a017

  日期：1983.6
• US5496927A
  申请人：——

  公开号：US5496927A

  公开（公告）日：1996-03-05
• US5849866A
  申请人：——

  公开号：US5849866A

  公开（公告）日：1998-12-15