N-caproyl-L-Pro-OH | 86282-93-1

• 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: N-caproyl-L-Pro-OH
• 英文别名: N-hexanoyl-L-proline；L-Proline, 1-(1-oxohexyl)-；(2S)-1-hexanoylpyrrolidine-2-carboxylic acid
• CAS: 86282-93-1
• 化学式: C₁₁H₁₉NO₃
• mdl: MFCD12795330
• 分子量: 213.277
• InChiKey: RTJVMTQLPNDWLB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-caproyl-L-Pro-OH 在 N-乙基吗啉 、 氨 、 氯甲酸异丁酯 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 N-caproyl-L-prolyl-L-tyrosine amide
  参考文献：
  名称：

  Design of N-Acylprolyltyrosine “Tripeptoid” Analogues of Neurotensin as Potential Atypical Antipsychotic Agents

  摘要：

  A series of N-acylprolyltyrosine amides was designed as tripeptoid analogues of neurotensin. The substituted dipeptides were tested in vivo for antidopamine activity by their ability to inhibit the apomorphine-induced climbing in mice and the dopamine-induced extrapolatory behavior impairment in rats. The N-acylprolyltyrosine amides structure-activity relationships have indicated the size of the N-acyl group and the configuration of amino acids that are important for the activity. Pie found that the bioactivity has been increased dramatically when the n-hydrocarbon chain on the N-acyl group was increased from four to five carbon atoms, The activity seems to reside exclusively in the L-Tyr diastereomers. All of the compounds tested were inactive in the cataleptogenic action and did not exhibit the acute toxicity even at doses 500-1000 times higher than ED50 climbing test, On this basis, the N-acylprolyltyrosine amides could potentially be a novel class of atypical antipsychotic agents.

  DOI：

  10.1021/jm970217c
• 作为产物：
  描述：

  己酰氯 、 L-脯氨酸 生成 N-caproyl-L-Pro-OH
  参考文献：
  名称：

  Design of N-Acylprolyltyrosine “Tripeptoid” Analogues of Neurotensin as Potential Atypical Antipsychotic Agents

  摘要：

  A series of N-acylprolyltyrosine amides was designed as tripeptoid analogues of neurotensin. The substituted dipeptides were tested in vivo for antidopamine activity by their ability to inhibit the apomorphine-induced climbing in mice and the dopamine-induced extrapolatory behavior impairment in rats. The N-acylprolyltyrosine amides structure-activity relationships have indicated the size of the N-acyl group and the configuration of amino acids that are important for the activity. Pie found that the bioactivity has been increased dramatically when the n-hydrocarbon chain on the N-acyl group was increased from four to five carbon atoms, The activity seems to reside exclusively in the L-Tyr diastereomers. All of the compounds tested were inactive in the cataleptogenic action and did not exhibit the acute toxicity even at doses 500-1000 times higher than ED50 climbing test, On this basis, the N-acylprolyltyrosine amides could potentially be a novel class of atypical antipsychotic agents.

  DOI：

  10.1021/jm970217c

文献信息

• Repurposing the 3‐Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
  作者：Mengyi Zhu、Lijuan Wang、Jing He

  DOI：10.1002/anie.202010042

  日期：2021.1.25

  molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate‐forming enzyme that adenylates a unique building block, 3‐isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile

  微生物天然产物的基因组挖掘使化学家不仅能够发现具有新颖骨架的生物活性分子，而且能够识别催化多种化学反应的酶。探索这些生物合成酶的底物混杂性和催化机理有助于开发潜在的生物催化剂。SFAB是一种形成酰基腺苷酸的酶，可在由硫链霉菌产生的二异腈自然产物SF2768的生物合成途径中，对独特的结构单元3-异氰基丁酸进行腺苷酸化。，并且该AMP连接酶被证明可以接受各种短链脂肪酸（SCFA）。在本文中，我们将SFAB重新用于催化那些SCFA与各种胺或硫醇亲核试剂之间的酰胺化或硫酯化反应，从而提供了另一种酶促方法来体外制备相应的酰胺和硫酯。
• Amine derivatives for the treatment of apoptosis
  申请人：——

  公开号：US20030216427A1

  公开（公告）日：2003-11-20

  The present invention is related to substituted amine derivatives notably for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such amine derivatives of formula (I). Said substituted amine derivatives are efficient modulators, in particular inhibitors, of the Bax function and/or activation. The present invention is furthermore related to novel substituted amine derivatives as well as methods of their preparation.

  本发明涉及替代胺衍生物，特别是用作药用活性化合物的替代胺衍生物，以及包含该式（I）的胺衍生物的药物配方。所述替代胺衍生物是Bax功能和/或激活的高效调节剂，特别是抑制剂。本发明还涉及新型替代胺衍生物以及其制备方法。
• 4H-3,1-benzoxazin-4-one derivative
  申请人：Japan Tobacco, Inc.

  公开号：US05204462A1

  公开（公告）日：1993-04-20

  4H-3,1-benzoxazin-4-one derivatives represented by formula (I) below: ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a lower alkyl group, a lower alkylthioalkyl group, or a lower alkanesulfinylalkyl group, R.sup.3 represents a hydrogen atom a hydroxyl group, a lower alkoxy group, or a lower acyloxy group, X represents an amino acid residue selected from the group consisting of alanine, valine, and phenylalanine, n represents an integer of 0, 1, or 2, and Y means a substituent selected from the group consisting of an alkanoyl group having 2 to 6 carbon atoms which may be substituted by a phenyl group, a benzyloxycarbonyl group, a lower alkoxycarbonyl group, a cinnamoyl group, and a methoxysuccinyl group. These derivatives exhibit a strong serine protease inhibiting effect, and are useful as effective components of agents for preventing and curing diseases caused by the excessive effect of serine proteases, e.g., pneumonia, pulmonary emphysema, fibroid lung, bronchitis, arthritis, pancreatitis, nephritis, shock, sepsis, and arteriosclerosis.

  以下是式子（I）所代表的4H-3,1-苯并噻唑-4-酮衍生物： 其中，R1代表较低的烷基，R2代表较低的烷基，较低的硫代烷基或较低的烷基磺酰基烷基，R3代表氢原子，羟基，较低的烷氧基或较低的酰氧基，X代表从丙氨酸，缬氨酸和苯丙氨酸中选择的氨基酸残基，n代表0、1或2的整数，Y代表从2到6个碳原子的脂肪酰基，可以被苯基取代，苄氧羰基，较低的烷氧羰基，肉桂酰基和甲氧基琥珀酰基等取代基。这些衍生物表现出强烈的丝氨酸蛋白酶抑制作用，并且可作为预防和治疗由丝氨酸蛋白酶过度作用引起的疾病的有效成分，例如肺炎，肺气肿，纤维性肺，支气管炎，关节炎，胰腺炎，肾炎，休克，败血症和动脉硬化等。
• NOVEL 4H-3,1-BENZOXAZIN-4-ONE DERIVATIVE
  申请人：Japan Tobacco Inc.

  公开号：EP0480044A1

  公开（公告）日：1992-04-15

  A 4H-3,1-benzoxazin-4-one derivative of general formula (I), which has a potent serine protease inhibitory action and is useful as the active ingredient of drugs for preventing and treating pneumonia, pulmonary emphysema, pulmonary fibrosis, bronchitis, arthritis, pancreatitis, nephritis, shock, sepsis, arteriosclerosis, etc.; wherein R¹ represents lower alkyl; R² represents lower alkyl, lower alkylthioalkyl or lower alkanesulfinylalkyl; R³ represents hydrogen, hydroxyl, lower alkoxy or lower acyloxy; X represents a residue of an amino acid selected from the group consisting of alanine, valine and phenyl-alanine; n is an integer of 0, 1 or 2; and Y represents a substituent selected from the group consisting of C₂ to C₆ alkanoyl optionally substituted with phenyl, benzyloxycarbonyl, lower alkoxycarbonyl, cinnamoyl and methoxysuccinoyl.

  一种通式(I)的4H-3,1-苯并恶嗪-4-酮衍生物，它具有强效的丝氨酸蛋白酶抑制作用，可作为预防和治疗肺炎、肺气肿、肺纤维化、支气管炎、关节炎、胰腺炎、肾炎、休克、败血症、动脉硬化等药物的活性成分。其中 R¹ 代表低级烷基；R² 代表低级烷基、低级烷硫基烷基或低级烷磺基烷基；R³ 代表氢、羟基、低级烷氧基或低级酰氧基；X 代表选自丙氨酸、缬氨酸和苯丙氨酸的氨基酸残基；n 是 0、1 或 2 的整数；以及 Y 代表选自由苯基、苄氧羰基、低级烷氧羰基、肉桂酰基和甲氧基琥珀酰基取代的 C₂ 至 C₆ 烷酰基组成的取代基。
• MOISTURIZER AND COSMETIC CONTAINING SAME
  申请人：Ajinomoto Co., Inc.

  公开号：EP3192493A1

  公开（公告）日：2017-07-19

  The present invention provides a composition containing (A) and (B), which shows a decreased peculiar odor of acylproline and a salt thereof, has a moist feeling and is superior in the stability: (A) acylproline represented by the formula (1) or a salt thereof (wherein an acyl group represented by R1-CO- is an acyl group induced from saturated or unsaturated fatty acid having 3 - 23 carbon atoms) (B) a zinc salt of pyrrolidone carboxylate.

  本发明提供了一种含有(A)和(B)的组合物，该组合物显示出丙烯基脯氨酸及其盐的特殊气味减弱，具有湿润感和优越的稳定性： (A) 由式(1)代表的丙烯基脯氨酸或其盐(其中由 R1-CO- 代表的酰基是由具有 3 - 23 个碳原子的饱和或不饱和脂肪酸引起的酰基) (B) 吡咯烷酮羧酸锌盐。