N,N-dibenzylglutamic acid α-benzyl ester | 1609011-54-2

• 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,N-dibenzylglutamic acid α-benzyl ester
• 英文别名: (4S)-4-(dibenzylamino)-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 1609011-54-2
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: GFBUZHDAVSMSEE-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dibenzylglutamic acid α-benzyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 tert-butyl (3S,12bR)-3-(dibenzylamino)-4-oxo-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizine-12-carboxylate
  参考文献：
  名称：

  Synthesis of Quinolizidinone and Indolizidinone Using N-Acyliminium Ion Cyclization and a One-Pot Procedure for Preparation of Benzoquinolizidinone

  摘要：

  DOI：

  10.3987/com-13-12917
• 作为产物：
  描述：

  L-谷氨酸 、 溴甲苯 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以73%的产率得到N,N-dibenzylglutamic acid α-benzyl ester
  参考文献：
  名称：

  Synthesis and antiproliferative activity of glutamic acid-based dipeptides

  摘要：

  A small and focused library of 22 dipeptides derived from N,N-dibenzylglutamic acid alpha- and gamma-benzyl esters was prepared in a straightforward manner. The evaluation of the antiproliferative activity in the human solid tumor cell lines HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast), and WiDr (colon) provided gamma-glutamyl methionine (GI(50) = 6.0-41 mu M) and alpha-glutamyl proline (GI(50) = 7.5-18 mu M) as lead compounds. In particular, glutamyl serine and glutamyl proline dipeptides were more active in the resistant cancer cell line WiDr than the conventional anticancer drugs cisplatin and etoposide. Glutamyl tryptophan dipeptides did not affect cell growth of HBL-100, while in T-47D cells, proliferation was inhibited. This result might be attributed to the inhibition of the ATB(0,+) transporter.

  DOI：

  10.1007/s00726-015-1987-0

文献信息

• Direct Synthesis of Polybenzylated Glutamic Acid Monoesters: Disambiguation of N,N-Dibenzylglutamic Acid α- and γ-Benzyl Esters
  作者：José Padrón、Gastón Silveira-Dorta、Víctor Martín

  DOI：10.1055/s-0034-1378532

  日期：——
• Synthesis of Quinolizidinone and Indolizidinone Using N-Acyliminium Ion Cyclization and a One-Pot Procedure for Preparation of Benzoquinolizidinone
  作者：Punlop Kuntiyong、Nuanpan Piboonsrinakara、Pijitra Bunrod、Duangkamol Namborisut、Sunisa Akkarasamiyo、Poramate Songthammawat、Chitlada Hemmara、Artid Buaphan、Boonsong Kongkathip

  DOI：10.3987/com-13-12917

  日期：——
• Synthesis and antiproliferative activity of glutamic acid-based dipeptides
  作者：Gastón Silveira-Dorta、Víctor S. Martín、José M. Padrón

  DOI：10.1007/s00726-015-1987-0

  日期：2015.8

  A small and focused library of 22 dipeptides derived from N,N-dibenzylglutamic acid alpha- and gamma-benzyl esters was prepared in a straightforward manner. The evaluation of the antiproliferative activity in the human solid tumor cell lines HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast), and WiDr (colon) provided gamma-glutamyl methionine (GI(50) = 6.0-41 mu M) and alpha-glutamyl proline (GI(50) = 7.5-18 mu M) as lead compounds. In particular, glutamyl serine and glutamyl proline dipeptides were more active in the resistant cancer cell line WiDr than the conventional anticancer drugs cisplatin and etoposide. Glutamyl tryptophan dipeptides did not affect cell growth of HBL-100, while in T-47D cells, proliferation was inhibited. This result might be attributed to the inhibition of the ATB(0,+) transporter.