N--L-tyrosine methyl ester hydrochloride | 57328-75-3

• 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: N--L-tyrosine methyl ester hydrochloride
• 英文别名: Gly-Tyr methyl ester hydrochloride；N-glycyl-L-tyrosine methyl ester; hydrochloride；N-Glycyl-L-tyrosin-methylester; Hydrochlorid；methyl(2S)-2-(2-aminoacetamido)-3-(4-hydroxyphenyl)propanoatehydrochloride；methyl (2S)-2-[(2-aminoacetyl)amino]-3-(4-hydroxyphenyl)propanoate;hydrochloride
• CAS: 57328-75-3
• 化学式: C₁₂H₁₆N₂O₄*ClH
• 分子量: 288.731
• InChiKey: IPOMLJRDALKBAM-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N--L-tyrosine methyl ester hydrochloride 、 (2S)-2-[[(Z)-2-benzamido-3-[(5-ethoxycarbonyl-2-methylsulfanylpyrimidin-4-yl)amino]prop-2-enoyl]amino]-3-phenylpropanoic acid 在 N-甲基吗啉 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 作用下， 生成 4-{(Z)-2-Benzoylamino-2-[(S)-1-({[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-vinylamino}-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  在肽合成中，N-保护基团是2-苄基-2-乙氧基羰基乙烯基-1和2-苯甲酰基氨基-2-甲氧基-羰基乙烯基-1 。它们在合成含N末端3-杂芳基氨基-2,3-脱氢丙氨酸的脱氢肽衍生物中的应用†

  摘要：

  2-苯甲酰基-3-二甲基氨基丙酸乙酯（6）和2-苯甲酰基氨基-3-二甲基氨基丙酸甲酯（46）被用作保护2-苯甲酰基-2-乙氧基羰基乙烯基-1和2-苯甲酰基氨基-2的氨基的试剂。肽合成中的-甲氧基羰基乙烯基。2-苯甲酰基-3-二甲基氨基丙酸乙酯（6）与α-氨基酸的反应得到N-（2-苯甲酰基-2-乙氧基羰基乙烯基-1）-α-氨基酸13-19。将它们与各种氨基酸酯偶联，形成N-（2-苯甲酰基-2-乙氧基羰基-乙烯基-1）保护的二肽酯20-31。通过肼一盐酸盐或羟胺盐酸盐去除2-苯甲酰基-2-乙氧基羰基乙烯基-1基团，可以高收率得到二肽酯32-41的氢氯化物。类似地，用甘氨酸取代2-苯甲酰基氨基-3-二甲基氨基丙酸甲酯（46）中的二甲基氨基得到N-（2-苯甲酰基氨基-2-甲氧基碳原子-乙烯基-1）甘氨酸（47），其与甘氨酸乙酯偶联得到N- [ N-（2-苯甲酰基氨基-2-甲氧基羰基乙烯基-1）甘氨酰]甘氨酸乙酯（48）。用2-氨基-4

  DOI：

  10.1002/jhet.5570340128
• 作为产物：
  描述：

  N-Phthaloyl-glycyl-tyrosin-methylester 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 N--L-tyrosine methyl ester hydrochloride
  参考文献：
  名称：

  Novel thiazolidinedione-5-acetic-acid-peptide hybrid derivatives as potent antidiabetic and cardioprotective agents

  摘要：

  Thiazolidinediones (TZDs) are one of the important clinically established antidiabetic agents. Aminoacid and peptides have an advantage of better target selectivity and specificity. As hybrids, they also improved absorption and showed better bioavailability, which in turn makes them safer. Hence, here an effort has been made to synthesize hybrids of thiazolidinedione with amino-acids and peptides and evaluate their antidiabetic and cardioprotective effect in streptozotocin-nicotinamide (STZ-NA) induced Type 2 diabetes mellitus (T2DM) rat models.A series of 14 thiazolidinedione-5-acetic acid hybrids with of different amino-acids and peptide combinations were synthesized, characterized and further screened for antidiabetic and cardioprotective activity.Among all, six compounds T1 (SSDMA1), T4 (SSDMA4), T5 (SSDMA5), T7 (SDMA13), T9 (SSDMA15) and T13 (SSDMA49) showed better antioxidant activity and comparable % glucose uptake by yeast cells.Hence, the in vivo antidiabetic screening was done for these six compounds. Among all six T1, T7, T13 showed significant blood glucose level decrease compared to standard pioglitazone HCl. Also T1, T7 and T13 showed better antioxidant activity with lower IC50 value than standard ascorbic acid, and hence in vivo cardioprotective studies were done for these. The ECG studies showed that T1 (SSDMA1) and T7 (SSDMA13) were better effective than SDMA49 (T13) in restoring the normal functioning of the heart, thus may help in preventing the development of diabetic cardiomyopathy (DCM) and controlling T2DM. (C) C 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biopha.2017.01.160

文献信息

• 124. Studies in the azole series. Part XXVI. The action of bases on 2-thio-4-methyl-5-thiazolidone
  作者：A. H. Cook、A. L. Levy

  DOI：10.1039/jr9500000642

  日期：——