4-[(4-methylbenzoyl)amino]butanoic acid | 223465-84-7

• 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: 4-[(4-methylbenzoyl)amino]butanoic acid
• 英文别名: 4-(N-(4-Methylphenylcarbonyl)amino)butyric acid；N-(p-toluoyl)-4-aminobutyric acid
• CAS: 223465-84-7
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD08442181
• 分子量: 221.256
• InChiKey: ROOXOEPLHGAHAX-UHFFFAOYSA-N

物化性质

• 沸点：
  464.0±38.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(4-methylbenzoyl)amino]butanoic acid 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (-)-N-(4-hydroxyamino-3-hydroxymethyl-4-oxobutyl)-4-methylbenzamide
  参考文献：
  名称：

  Novel matrix metalloproteinase inhibitors: Generation of lead compounds by the in silico fragment-based approach

  摘要：

  Generation of structurally new matrix metalloproteinase inhibitors was successfully carried out using an in silico technique. In order to identify the small fragment interacting with residues in the S1' pocket of MMP-1 through hydrogen bonds, we performed in silico screening using the LUDI program. As a result, acetyl-L-alanyl-(N-methyl)amide (AC-L-Ala-NHMe) was selected to link with another fragment, hydroxamic acid that interacted with catalytic zinc. By this approach, the L-glutamic acid derivative 2b was discovered to be a new type of matrix metalloproteinase inhibitor. Further transformation to reduce its peptidic nature and improve activity yielded nonpeptidic lead compounds as inhibitors of MMP-1, -2, -3, and -9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.051
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 4-氨基丁酸 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以90%的产率得到4-[(4-methylbenzoyl)amino]butanoic acid
  参考文献：
  名称：

  新型金属蛋白酶抑制剂的设计与合成。

  摘要：

  合成了一系列的N-苯甲酰基4-氨基丁酸异羟肟酸酯类似物，并将其评估为基质金属蛋白酶抑制剂。合成工作的重点是使用容易获得的起始原料对4-氨基丁酸部分进行化学修饰。这样，使用可商购的起始原料例如4-氨基丁酸，（+）-和（-）-苹果酸以及D-和L-谷氨酸衍生物进行化学修饰。在测试的化合物中，衍生自L-谷氨酸的N- [4-（苯并呋喃-2-基）苯甲酰基] 4-氨基-4S-羟甲基丁酸异羟肟酸酯与MMP-2和MMP-9相比，对MMP-2和MMP-9的抑制作用更强。分别衍生自（-）-苹果酸的相应2S-羟基类似物或3S-羟基类似物。提出了构效关系研究。

  DOI：

  10.1016/j.bmc.2006.03.032

文献信息

• Aminobutyric acid derivatives
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06420427B1

  公开（公告）日：2002-07-16

  An aminobutyric acid derivative of the formula (I): (wherein all symbols are as defined in the specification) and salt thereof. salt thereof. The compounds of the formula (I) possess an inhibitory activity on matrix metalloproteinase and are useful for prevention and/or treatment of diseases, for example, rheumatoid diseases, arthrosteitis, unusual bone resorption, osteoporosis, periodontitis, interstitial nephritis, arteriosclerosis, pulmonary emphysema, cirrhosis, cornea injury, metastasis of, invasion of or growth of tumor cells, autoimmune disease (e.g. Crohn's disease, Sjogren's syndrome), disease caused by vascular emigration or infiltration of leukocytes, arterialization, multiple sclerosis, aorta aneurysm, endometriosis.

  化合物的公式(I)为氨基丁酸衍生物：（其中所有符号均如规范中定义），以及其盐。公式(I)的化合物具有对基质金属蛋白酶的抑制活性，并可用于预防和/或治疗疾病，例如风湿性疾病，关节炎，异常骨吸收，骨质疏松症，牙周炎，间质性肾炎，动脉硬化，肺气肿，肝硬化，角膜损伤，肿瘤细胞的转移、侵袭或生长，自身免疫性疾病（例如克隆病，Sjogren综合征），由血管移民或白细胞浸润引起的疾病，动脉化，多发性硬化症，主动脉瘤，子宫内膜异位症。
• AMINOBUTANOIC ACID DERIVATIVES
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1024134A1

  公开（公告）日：2000-08-02

  An aminobutyric acid derivative of the formula (I): (wherein all symbols are as defined in the specification) and salt thereof. salt thereof. The compounds of the formula (I) possess an inhibitory activity on matrix metalloproteinase and are useful for prevention and / or treatment of diseases, for example, rheumatoid diseases, arthrosteitis, unusual bone resorption, osteoporosis, periodontitis, interstitial nephritis, arteriosclerosis, pulmonary emphysema, cirrhosis, cornea injury, metastasis of, invasion of or growth of tumor cells, autoimmune disease (e.g. Crohn's disease, Sjogren's syndrome), disease caused by vascular emigration or infiltration of leukocytes, arterialization, multiple sclerosis, aorta aneurysm, endometriosis.

  式（I）的氨基丁酸衍生物： (其中所有符号如说明书中所定义）及其盐。 式（I）化合物对基质金属蛋白酶具有抑制活性，可用于预防和/或治疗疾病，例如类风湿病、关节炎、异常骨吸收、骨质疏松症、牙周炎、间质性肾炎、动脉硬化、肺气肿、肝硬化、角膜损伤、肿瘤细胞的转移、侵入或生长、自身免疫性疾病（如克罗恩病、Sj.如克罗恩病、Sjogren 综合症）、血管移位或白细胞浸润引起的疾病、动脉化、多发性硬化、主动脉瘤、子宫内膜异位症。
• APPLICATION OF ACYLATED DERIVATIVE OF AMINO ACID IN PREPARATION OF ANIMAL FEED ADDITIVE
  申请人：Peng, Xianfeng

  公开号：EP3878287A1

  公开（公告）日：2021-09-15

  The present invention provides a use of an acylated derivative of an amino acid in preparing animal feed additive. The acylated derivative of the amino acid or a racemate, stereoisomer, a geometric isomer, a tautomer, a solvate, and a feed-acceptable salt thereof of the present invention has a structure represented by formula (I). The acylated derivative of the amino acid or the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate, and the feed-acceptable salt thereof provided in the present invention may be used as an animal feed additive, and has a good effect of improving production performance of animals.

  本发明提供了一种氨基酸酰化衍生物在制备动物饲料添加剂中的用途。本发明的氨基酸酰化衍生物或其外消旋体、立体异构体、几何异构体、同分异构体、溶质和饲料可接受盐的结构由式（I）表示。 本发明提供的氨基酸的酰化衍生物或外消旋物、立体异构体、几何异构体、同分异构体、溶出物及其饲料可接受盐可用作动物饲料添加剂，并具有提高动物生产性能的良好效果。
• Discovery of a new chemical lead for a matrix metalloproteinase inhibitor
  作者：Masahiro Ikura、Shingo Nakatani、Shingo Yamamoto、Hiromu Habashita、Tsuneyuki Sugiura、Kanji Takahashi、Koji Ogawa、Hiroyuki Ohno、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2006.01.059

  日期：2006.6

  A series of N-benzoyl gamma-aminobutyric hydroxamic acids were synthesized and evaluated as matrix metalloproteinase inhibitors. First, we focused on chemical modification of the N-benzoyl residue. Introduction of electron-rich para-substituents was effective to increase the inhibitory activity. Especially, some of the analogs with relatively more planar N-acyl residues, such as 10 and 11, demonstrated more potent activity. Second, chemical modification of the gamma-aminobutyric hydroxamic acid moiety was carried out to optimize the three-dimensional arrangement of the two pharmacophores (hydroxamic acid and N-acyl residues). Among the tested, the gamma-aminobutyric hydroxamic acid moiety was found to be the best spacer for connecting the above-mentioned two pharmacophores. Synthesis and structure-activity relationships are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
• US4757066A
  申请人：——

  公开号：US4757066A

  公开（公告）日：1988-07-12