N-t-butoxycarbonyl-L-t-butylglycine p-nitrophenyl ester | 374783-12-7

• 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-t-butoxycarbonyl-L-t-butylglycine p-nitrophenyl ester
• 英文别名: 4-nitrophenyl N-t-Boc-L-tert-butylglycinate；(4-nitrophenyl) (2S)-3,3-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 374783-12-7
• 化学式: C₁₇H₂₄N₂O₆
• 分子量: 352.387
• InChiKey: NPBHDZDQBXDOSZ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-t-butoxycarbonyl-L-t-butylglycine p-nitrophenyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N¹-spermine L-tert-butylglycinyl amide tetrahydrochloride
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040
• 作为产物：
  描述：

  对硝基苯酚 、 N-Boc-L-叔亮氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以85%的产率得到N-t-butoxycarbonyl-L-t-butylglycine p-nitrophenyl ester
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040

文献信息

• Synthesis and DP-IV inhibition of cyano-pyrazoline derivatives as potent anti-diabetic agents
  作者：Jin Hee Ahn、Hye-Min Kim、Sun Ho Jung、Seung Kyu Kang、Kwang Rok Kim、Sang Dal Rhee、Sung-Don Yang、Hyae Gyeong Cheon、Sung Soo Kim

  DOI：10.1016/j.bmcl.2004.06.046

  日期：2004.9

  A new series of cyano-pyrazoline derivatives with a secondary amine at P-2 site was synthesized through achiral and chiral synthetic methods and evaluated for their ability to inhibit dipeptidyl peptidase IV (DP-IV). Compound 5i revealed good in vivo efficacy (ED50: 4.1 mg/kg; in vivo DP-IV inhibition). Also chiral derivative (11b) having (S)-configuration of compound 5i was found to be more potent. (C) 2004 Elsevier Ltd. All rights reserved.