(S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dimethoxyphenyl)propanoate | 128595-72-2

• 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: (S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dimethoxyphenyl)propanoate
• 英文别名: (-)-N-benzyloxycarbonyl-3,4-dimethoxy-L-phenylalanine methyl ester；methyl (2S)-3-(3,4-dimethoxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 128595-72-2
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: UGJXEFNBEBDLAV-INIZCTEOSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  537.4±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dimethoxyphenyl)propanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到(S)-3,4-二甲氧基苯基丙氨酸甲酯
  参考文献：
  名称：

  Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

  摘要：

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.048
• 作为产物：
  描述：

  N-benzyloxycarbonyl-L-dopa 在 potassium hydrogencarbonate 作用下， 以 丙酮 为溶剂， 以4.3 g的产率得到(S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dimethoxyphenyl)propanoate
  参考文献：
  名称：

  Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

  摘要：

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.048

文献信息

• Synthesis and positive inotropic effect of 1-alkyl- and 1-acyl-6,7-dimethoxy-3-dimethylamino-1,2,3,4-tetrahydroquinolines
  作者：F SANTANGELO、C CASAGRANDE、G MIRAGOLI、V VECCHIETTI

  DOI：10.1016/0223-5234(94)90110-4

  日期：——

  In the search for new positive inotropic agents we have investigated a series of 3-dimethylamino-1,2,3,4-tetrahydroquinolines with various substituents on the nitrogen of the quinoline ring. The N-isobutyryl derivative 20 (S903) was selected as the most interesting compound. Interestingly, while cardiac contractility was increased in vitro, heart rate was unchanged or slightly decreased. The positive inotropic activity was partly dependent on an indirect sympathomimetic effect. The (S) absolute configuration of the (-)enantiomer of S903 was established by correlation with (S)-L-dopa.
• ADAM, MICHAEL J.;PONCE, YOLANDA ZEA;BERRY, JOFFRE M.;HOY, KEVIN, J. LABELL. COMPOUNDS AND RADIOPHARM., 28,(1990) N, C. 155-166
  作者：ADAM, MICHAEL J.、PONCE, YOLANDA ZEA、BERRY, JOFFRE M.、HOY, KEVIN

  DOI：——

  日期：——