L-苯基丙氨酰氨基(3-甲基)丁烷 | 110755-29-8

• 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
• 中文名称: L-苯基丙氨酰氨基(3-甲基)丁烷
• 英文名称: L-phenylalanine isopentylamide
• 英文别名: L-phenylalanylamido(3-methyl)butane；N-(L-phenylalanyl)isopentylamine；N-(3-methylbutyl)-L-phenylalaninamide；(2S)-2-amino-N-(3-methylbutyl)-3-phenylpropanamide
• CAS: 110755-29-8
• 化学式: C₁₄H₂₂N₂O
• mdl: MFCD09725309
• 分子量: 234.341
• InChiKey: XFYCBJHUCMXATG-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-苯基丙氨酰氨基(3-甲基)丁烷 在 氢氧化钾 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 D-trans-epoxysuccinyl-L-phenylalanylamido(3-methyl)butane
  参考文献：
  名称：

  Iodo and diiodotyrosine epoxysuccinyl derivatives as selective inhibitors of cathepsin B

  摘要：

  Eight new analogs of L-trans-epoxysuccinyl-L-leucylamido(3-methyl)butane (E-64-c) containing Phe, Tyr, Tyr(I) or Tyr(I-2) in place of Leu, were synthesized and tested as inhibitors of papain, bovine spleen cathepsin B, calpain I and II from porcine red cells and porcine kidney, respectively. By use of kinetic methods, the new E-64 analogs proved to irreversibly inactivate both papain and cathepsin B via reversible enzyme-inhibitor intermediates EI. Second-order rate constants for inactivation were in the range 3500-55 100 M(-1)s(-1) for papain and 650-105 000 M(-1)s(-1) for cathepsin B. For the inactivation of calpain I and II they ranged between 250 and 2000 M(-1)s(-1) and were similar to those of the known E-64-c. The effectiveness of the amino acid contained in the inhibitors tested increased in the order Tyr(I) approximate to Tyr(I-2) < Tyr < Phe < Leu for papain and Phe < Tyr < Tyr(I)e Leu < Tyr(I-2) for cathepsin B inactivation. Replacement of the L with the D-trans-epoxysuccinyl unit caused a 10-100-fold decrease in inhibitor potencies.

  DOI：

  10.1016/0223-5234(93)90046-h
• 作为产物：
  描述：

  Z-Phe-O-COO-isoBu 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 L-苯基丙氨酰氨基(3-甲基)丁烷
  参考文献：
  名称：

  N-Haloacetyl-amino-acid amides as active-site-directed inhibitors of papain and cathepsin B

  摘要：

  A series of N-haloacetyl-amino-acid amides were synthesized and tested as models of cysteine-protease inhibitors. They irreversibly inactivated papain and cathepsin B via a reversible enzyme--inhibitor intermediate. Apparent second-order rate constants of inactivation ranging from 65 to 16 700 M-1 s-1 were observed. Reactivity against papain, as compared to glutathione, was increased 16 400-fold for N-bromoacetyl-leucine isopentylamide and 25 700-fold for the corresponding iodoacetyl derivative; these increases are probably due to proximity effects. No inhibition of trypsin, chymotrypsin and porcine pancreatic elastase was observed. Haloacetamides represent an interesting class of easily synthesized, efficient. irreversible inhibitors of cysteine proteases, which have low non-specific alkylating properties.

  DOI：

  10.1016/0223-5234(92)90018-v

文献信息

• Aziridine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05668128A1

  公开（公告）日：1997-09-16

  The present invention relates to a compound of the formula: ##STR1## wherein R.sub.1 and Q are independently an optionally esterified or amidated carboxyl group; R.sub.2 is hydrogen, an acyl group or an optionally substituted hydrocarbon residue; X is a divalent hydrocarbon residue which may be substituted; or a salt thereof, which is useful as prophylactic and therapeutic agents of bone diseases and as agents for inhibiting thiol protease.

  本发明涉及一种化合物，其化学式为：##STR1## 其中R.sub.1和Q分别是可选择酯化或酰胺化的羧基；R.sub.2是氢、酰基或可选择取代的碳氢残基；X是可能被取代的二价碳氢残基；或其盐，可用作预防和治疗骨疾病的药剂以及抑制硫醇蛋白酶的药剂。
• Design, synthesis and evaluation of 3-methylene-substituted indolinones as antimalarials
  作者：S. Praveen Kumar、Jiri Gut、Rita C. Guedes、Philip J. Rosenthal、Maria M.M. Santos、Rui Moreira

  DOI：10.1016/j.ejmech.2011.01.008

  日期：2011.3

  The design, synthesis and evaluation of 3-methylene-substituted indolinones as falcipain inhibitors and antiplasmodial agents are described. These compounds react readily with thiols via an addition-elimination mechanism, indicating their potential as cysteine protease inhibitors. Several indolinones containing a Leu-i-amyl recognition moiety were found to be moderate inhibitors of the Plasmodium falciparum

  描述，设计和合成的3-亚甲基取代的吲哚啉酮作为falcipain抑制剂和抗疟原虫剂。这些化合物通过加成消除机制容易与硫醇反应，表明它们作为半胱氨酸蛋白酶抑制剂的潜力。含有具有Leu-几个吲哚满酮我发现戊识别部分是适度抑制剂的恶性疟原虫半胱氨酸蛋白酶falcipain-2，但不相关的蛋白酶falcipain-3，和针对抗氯喹显示抗疟原虫活性恶性疟原虫W2在低微摩尔范围内的应变。将7-氯喹啉部分偶联至3-亚甲基取代的吲哚酮骨架上导致抗血浆活性的显着改善。
• The Bsmoc group as a novel scaffold for the design of irreversible inhibitors of cysteine proteases
  作者：Jim Iley、Rui Moreira、Luísa Martins、Rita C. Guedes、Cláudio M. Soares

  DOI：10.1016/j.bmcl.2006.02.007

  日期：2006.5

  not significantly affected by the nature of the carboxylic or carbamic acid leaving group. These Michael acceptors are irreversible inhibitors of the cysteine proteases papain and human liver cathepsin B, displaying first-order kinetics with respect to inhibitor concentration. In contrast, none of the Bsmoc derivatives inhibited porcine pancreatic elastase, a serine protease.

  1,1-二氧代苯并[b]噻吩-2-基甲氧基羰基（Bsmoc）支架的氨基甲酸酯和酯衍生物可以通过迈克尔加成反应与巯基反应，其反应速率不受羧基或氨基甲酸离去基团性质的明显影响。这些迈克尔受体是半胱氨酸蛋白酶木瓜蛋白酶和人肝组织蛋白酶B的不可逆抑制剂，在抑制剂浓度方面表现出一级动力学。相反，没有Bsmoc衍生物抑制猪胰弹性蛋白酶，一种丝氨酸蛋白酶。
• Analgesic and/or opiate antagonist tripeptide amides and processes for
  申请人：Sterling Drug Inc.

  公开号：US04658013A1

  公开（公告）日：1987-04-14

  A genus of tripeptide amides and fifteen species thereof of Examples 4-18, which are useful as analgesics and/or opiate antagonists, three processes for preparation thereof, pharmaceutical compositions thereof, and the three tripeptide amide species of Examples 1-3, which are not within the genus and are useful as analgesics and/or opiate antagonists, are disclosed.

  本文披露了一种三肽酰胺属及其15种物种（示例4-18），它们可用作镇痛剂和/或阿片受体拮抗剂，以及三种制备方法、制药组合物。此外，还披露了三种不属于该属的三肽酰胺物种（示例1-3），它们也可用作镇痛剂和/或阿片受体拮抗剂。
• 1,3,2-DIOXATHIOLANE OXIDE DERIVATIVE
  申请人：Japan Tobacco Inc.

  公开号：EP0460239A1

  公开（公告）日：1991-12-11

  A 1,3,2-dioxathiolane oxide derivative of general formula (I) wherein x represents -S(O)- or -S(O)₂-; R¹ represents hydrogen, alkali metal atom, benzyl or lower alkyl; R² represents lower alkyl which may be substituted by methylthio, or benzyl; and R³ and R⁴ may be the same or different from each other and each represents hydrogen, C₁ to C₁₀ alkyl, guanidyl-substituted lower alkyl, C₃ to C₆ cycloalkyl, phenyl, benzyl or phenoethyl, or R³ and R⁴ are combined together to represent alkylene.

  通式(I)的 1,3,2-二氧代硫杂环戊烷氧化物衍生物 其中 x 代表-S(O)-或-S(O)₂-；R¹ 代表氢、碱金属原子、苄基或低级烷基；R² 代表可被甲硫基或苄基取代的低级烷基；和 R³ 和 R⁴ 可以彼此相同或不同，并且各自代表氢、C₁ 至 C₁₀ 烷基、胍基取代的低级烷基、C₃ 至 C₆ 环烷基、苯基、苄基或苯乙基，或者 R³ 和 R⁴ 结合在一起代表亚烷基。