N-benzyloxycarbonyl-L-dopa | 73404-23-6

• 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-benzyloxycarbonyl-L-dopa
• 英文别名: N-benzyloxycarbonyl-3,4-dimethoxy-L-phenylalanine；(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3,4-dimethoxyphenyl)propanoic acid；(2S)-3-(3,4-dimethoxyphenyl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 73404-23-6
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: SKYCRNVEWQXSSF-HNNXBMFYSA-N

物化性质

• 沸点：
  560.1±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  左旋多巴 、 氯甲酸苄酯 在 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 N-benzyloxycarbonyl-L-dopa
  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

• Design of a Small-Molecule Catalyst Using Intramolecular Cation−π Interactions for Enantioselective Diels−Alder and Mukaiyama−Michael Reactions:  <scp>l</scp>-DOPA-Derived Monopeptide·Cu(II) Complex
  作者：Kazuaki Ishihara、Makoto Fushimi

  DOI：10.1021/ol060651l

  日期：2006.4.1

  [reaction: see text] We have designed a small-molecule artificial metalloenzyme that is prepared in situ from Cu(OTf)(2) or Cu(NTf(2))(2) (1.0 equiv) and l-DOPA-derived monopeptide (1.1 equiv). This catalyst (2-10 mol %) is highly effective for the enantioselective Diels-Alder (DA) and Mukaiyama-Michael (MM) reactions with alpha,beta-unsaturated 1-acyl-3,5-dimethylpyrazoles. The present results demonstrate

  [反应：请参见文本]我们设计了一种小分子人工金属酶，该酶是从Cu（OTf）（2）或Cu（NTf（2））（2）（1.0当量）和l-DOPA衍生的单肽原位制备的（1.1当量）。该催化剂（2-10mol％）对于与α，β-不饱和的1-酰基-3，5-二甲基吡唑的对映选择性Diels-Alder（DA）和Mukaiyama-Michael（MM）反应是高度有效的。本结果表明，阳离子-pi相互作用可用于控制手性配体的侧臂的构象，并且单肽是易于调谐的仅包含一个手性中心的配体。
• 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.