N-maleyl-L-alanine | 39829-02-2

• 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-maleyl-L-alanine
• 英文别名: N-(3c-carboxy-acryloyl)-L-alanine；N-((S)-1-Carboxy-aethyl)-maleamidsaeure；N-(3c-Carboxy-acryloyl)-L-alanin；L-Alanin-maleamid；(Z)-4-[[(1S)-1-carboxyethyl]amino]-4-oxobut-2-enoic acid
• CAS: 39829-02-2
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: GNLCKFJPWPKISM-SWOZAWMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-maleyl-L-alanine 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 六甲基二硅氮烷 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 methyl N,N-maleoyl-L-alanyl-L-phenylalaninate
  参考文献：
  名称：

  Bodtke; Otto, Hans-Hartwig, Pharmazie, 2005, vol. 60, # 11, p. 803 - 813

  摘要：

  DOI：
• 作为产物：
  描述：

  马来酸酐 、 L-丙氨酸 以 溶剂黄146 为溶剂， 生成 N-maleyl-L-alanine
  参考文献：
  名称：

  Alkylating derivatives of amino acids and peptides. Synthesis of N-maleoylamino acids, [1-(N-maleoylglycyl)cysteinyl]oxytocin, and [1-(N-maleoyl-11-aminoundecanoyl)cysteinyl]oxytocin. Effects on vasopressin-stimulated water loss from isolated toad bladder

  摘要：

  A method for the preparation of N-maleoylamino acids and esters is reported. These compounds were shown to inhibit both the oxytocin-induced smooth muscle contraction in the isolated rat uterus and the vasopressin-induced water loss from the isolated toad bladder. The inhibitory ability of the maleimides in the toad bladder assay was found to be related to their corresponding partition coefficients by the equation: log 1/C = -0.055 (log P) 2 + 0.227 log P + 3.96. N-Maleoylamino acids can be coupled to peptides to form alkylating reagents which react rapidly with sulfhydryl groups. The synthesis of [1-(N-maleoylglycyl)cysteinyl]oxytocin (3) and [1=(N-maleoyl-11-aminoundecanoyl)cysteinyl]oxytocin (4) as potential affinity labeling reagents is described. These oxytocin analogs were shown to readily react with sulfhydryl-containing compounds; however, neither 3 nor 4 was seen to inhibit in the rat uterus assay at concentrations up to 3 times 10(-5)M. When tested on the mucosal and serosal surfaces of the toad bladder, assay inhibition was seen only on the mucosal surface. These results are discussed with respect to the possible existence of sulfhydryl groups at neurohypophyseal receptors.

  DOI：

  10.1021/jm00244a011

文献信息

• King et al., Journal of the Chemical Society, 1957, p. 873,879
  作者：King et al.

  DOI：——

  日期：——
• Chemosensory Receptor Ligand-Based Therapies
  申请人：Brown Martin R.

  公开号：US20130303466A1

  公开（公告）日：2013-11-14

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administering a composition comprising a chemosensory receptor ligand. Also provided herein are chemosensory receptor ligand compositions and methods for the preparation thereof for use in the methods of the present invention.
• [EN] CHEMOSENSORY RECEPTOR LIGAND-BASED THERAPIES<br/>[FR] THÉRAPIES À BASE DE LIGAND DE RÉCEPTEUR CHIMIOSENSIBLE
  申请人：ELCELYX THERAPEUTICS INC

  公开号：WO2012054527A2

  公开（公告）日：2012-04-26

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administering a composition comprising a chemosensory receptor ligand. Also provided herein are chemosensory receptor ligand compositions and methods for the preparation thereof for use in the methods of the present invention.