N--L-glutamine ethyl ester | 110694-61-6

• 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--L-glutamine ethyl ester
• 英文别名: ethyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 110694-61-6
• 化学式: C₁₂H₂₂N₂O₅
• 分子量: 274.317
• InChiKey: GZHKGEWJTKFZJM-QMMMGPOBSA-N

物化性质

• 沸点：
  468.9±40.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  107.72
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N--L-glutamine ethyl ester 在 potassium dihydrogenphosphate 、 potassium tert-butylate 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 水 、 叔丁醇 为溶剂， 反应 30.0h， 生成 N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester
  参考文献：
  名称：

  A study of the delivery-targeting concept applied to antineoplasic drugs active on human osteosarcoma. I. Synthesis and biological activity in nude mice carrying human osteosarcoma xenografts of gem-bisphosphonic methotrexate analogues

  摘要：

  With the aim of verifying the concept of osteotic vectorisation, synthesis of three methotrexate (MTX) gem-diphosphonic analogues (compounds A, B and C) was performed. These molecules were tested on BALB/c and NIH III mice previously grafted with subcutaneous implants of OHS, TTX p7 and/or TTX p11 human osteosarcoma cell lines. Antineoplasic activity of compound B and C (active compounds) was compared to the activity for MTX alone and to activity of compound A (inactive compound). Compounds B and C exhibited an increased antineoplasic activity compared to MTX alone and to compound A. At equimolar doses, compound B was found to be 5-6-fold more active than MTX given alone. We have discussed the concept of osteotic vectorisation of compound B, which could be regarded as a prodrug.

  DOI：

  10.1016/0223-5234(92)90117-j
• 作为产物：
  描述：

  L-谷氨酰胺 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 97.0h， 生成 N--L-glutamine ethyl ester
  参考文献：
  名称：

  A study of the delivery-targeting concept applied to antineoplasic drugs active on human osteosarcoma. I. Synthesis and biological activity in nude mice carrying human osteosarcoma xenografts of gem-bisphosphonic methotrexate analogues

  摘要：

  With the aim of verifying the concept of osteotic vectorisation, synthesis of three methotrexate (MTX) gem-diphosphonic analogues (compounds A, B and C) was performed. These molecules were tested on BALB/c and NIH III mice previously grafted with subcutaneous implants of OHS, TTX p7 and/or TTX p11 human osteosarcoma cell lines. Antineoplasic activity of compound B and C (active compounds) was compared to the activity for MTX alone and to activity of compound A (inactive compound). Compounds B and C exhibited an increased antineoplasic activity compared to MTX alone and to compound A. At equimolar doses, compound B was found to be 5-6-fold more active than MTX given alone. We have discussed the concept of osteotic vectorisation of compound B, which could be regarded as a prodrug.

  DOI：

  10.1016/0223-5234(92)90117-j

文献信息

• Kinetic resolution of esters via metal catalyzed methanolysis reactions
  作者：Christopher I. Maxwell、Kalpa Shah、Pavel V. Samuleev、Alexei A. Neverov、R. Stan Brown

  DOI：10.1039/b805236k

  日期：——

  2-diaminocyclohexane (MePyr-chxn, 4); and c) 2,6-pyridyldicarboxaldehyde and (1R),(2R)-trans-1,2-diaminocyclohexane ((Pyr-R,R'-chxn)(2), 5) have been screened for their utility to promote kinetic resolution via metal catalyzed alcoholyses of the p-nitrophenyl esters of chiral D- and L-Boc-protected glutamine and phenylalanine. Solvents were varied to optimize the kinetic selectivity values, defined as

  席夫碱加合物的一些手性镧系配合物：a）双（2-吡啶基甲醛）和（1R），（2R）-反式-1,2-二氨基环己烷（Pyr-R，R'-chxn：3）；b）6-甲基-2-吡啶基甲醛和（1R），（2R）-反式1,2-二氨基环己烷（MePyr-chxn，4）; c）已经筛选了2,6-吡啶基二甲醛和（1R），（2R）-反式-1,2-二氨基环己烷（（Pyr-R，R'-chxn）（2），5）的效用以促进动力学通过金属催化的手性D-和L-Boc保护的谷氨酰胺和苯丙氨酸的对硝基苯基酯的拆分。改变溶剂以优化动力学选择性值，定义为k（2）（L）/ k（2）（D）或k（2）（D）/ k（2）（L），用于甲醇分解和某些反应情况下，这些底物的乙醇解作用。在环境温度下，发现由3：Yb（3+）催化的Boc-Gln-OPNP的乙醇化选择性最高：（（-）OEt）（k（2）（L）/ k（2）（D）= 7.2）。对于Boc-Phe-OPNP的最大选择性是k（2）（D）/
• Synthesis of amino acid esters by papain
  作者：D. Cantacuzène、F. Pascal、C. Guerreiro

  DOI：10.1016/s0040-4020(01)81493-9

  日期：1987.1
• CANTACUZENE, D.;PASCAL, F.;GUERREIRO, C., TETRAHEDRON, 43,(1987) N 8, 1823-1826
  作者：CANTACUZENE, D.、PASCAL, F.、GUERREIRO, C.

  DOI：——

  日期：——