N-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide | 923563-62-6

• 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-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide
• 英文别名: [(R)-1-(methoxy-methyl-carbamoyl)-2-o-tolyl-ethyl]-carbamic acid tert-butyl ester；tert-butyl N-[(2R)-1-[methoxy(methyl)amino]-3-(2-methylphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 923563-62-6
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: GEHYPVUPDSRPOF-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 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：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide 在 lithium aluminium tetrahydride 、 二甲基硫 、 三氟甲磺酸二丁硼 、 双氧水 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid
  参考文献：
  名称：

  Deglycobleomycin A6 analogues modified in the methylvalerate moiety

  摘要：

  Previous studies have indicated that the methylvalerate subunit of bleomycin (BLM) plays an important role in facilitating DNA cleavage by BLM and deglycoBLM. Eleven methylvalerate analogues have been synthesized and incorporated into deglycoBLM congeners by the use of solid-phase synthesis. The effect of the valerate moiety in the deglycoBLM analogues has been studied by comparison with the parent deglycoBLM A(5) using supercoiled DNA relaxation and sequence-selective DNA cleavage assays. All of the deglycoBLM analogues were found to effect the relaxation of the plasmid DNA. Those analogues having aromatic C4-substituents exhibited cleavage efficiency comparable to that of deglycoBLM A(5). Some, but not all, of the deglycoBLM analogues were also capable of mediating sequence-selective DNA cleavage. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.04.047
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 BOC-D-2-甲基苯丙氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 以97%的产率得到N-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide
  参考文献：
  名称：

  Deglycobleomycin A6 analogues modified in the methylvalerate moiety

  摘要：

  Previous studies have indicated that the methylvalerate subunit of bleomycin (BLM) plays an important role in facilitating DNA cleavage by BLM and deglycoBLM. Eleven methylvalerate analogues have been synthesized and incorporated into deglycoBLM congeners by the use of solid-phase synthesis. The effect of the valerate moiety in the deglycoBLM analogues has been studied by comparison with the parent deglycoBLM A(5) using supercoiled DNA relaxation and sequence-selective DNA cleavage assays. All of the deglycoBLM analogues were found to effect the relaxation of the plasmid DNA. Those analogues having aromatic C4-substituents exhibited cleavage efficiency comparable to that of deglycoBLM A(5). Some, but not all, of the deglycoBLM analogues were also capable of mediating sequence-selective DNA cleavage. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.04.047

文献信息

• Pyridine Derivatives as Dipeptedyl Peptidase Inhibitors
  申请人：Blaszczak Larry Chris

  公开号：US20080214616A1

  公开（公告）日：2008-09-04

  The present invention is directed to compounds of formula (I) or a pharmaceutically acceptable salt thereof; wherein A is (1); X is selected from CH, CF and N; R5 is selected from H, C 1 -C 6 fluoroalkyl, and —OR12; R9 is selected from H —NR13C(O)R14 and —C(O)NR10R11; R12 is selected from H, C 1 -C 6 alkyl and C 3 -C 6 cycloalkyl, for use as inhibitors of the DPP-IV enzyme in the treatment or prevention of conditions including Type II diabetes.

  本发明涉及公式（I）的化合物或其药学上可接受的盐；其中A为（1）；X选自CH，CF和N；R5选自H，C1-C6氟烷基和—OR12；R9选自H，—NR13C（O）R14和—C（O）NR10R11；R12选自H，C1-C6烷基和C3-C6环烷基，用作DPP-IV酶的抑制剂，用于治疗或预防包括2型糖尿病在内的疾病。
• PYRIDINE DERIVATIVES AS DIPEPTEDYL PEPTIDASE INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1912946B1

  公开（公告）日：2009-05-27
• US8133907B2
  申请人：——

  公开号：US8133907B2

  公开（公告）日：2012-03-13
• [EN] PYRIDINE DERIVATIVES AS DIPEPTEDYL PEPTIDASE INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINE EN TANT QU'INHIBITEURS DE DIPEPTEDYL PEPTIDASE
  申请人：LILLY CO ELI

  公开号：WO2007015767A1

  公开（公告）日：2007-02-08

  [EN] The present invention is directed to compounds of formula (I) or a pharmaceutically acceptable salt thereof; wherein A is (1); X is selected from CH, CF and N; R5 is selected from H, C₁-C₆ alkyl, C₁-C₆ fluoroalkyl, and -OR12; R9 is selected from H -NR13C(O)R14 and -C(O)NR10R11; R12 is selected from H, C₁-C₆ alkyl and C₃-C₆ cycloalkyl, for use as inhibitors of the DPP-IV enzyme in the treatment or prevention of conditions including Type II diabetes.
  [FR] La présente invention concerne des composés de formule I : ou un sel pharmaceutiquement acceptable de ceux-ci ; dans laquelle A est égal à X est choisi parmi CH, CF et N ; R5 est choisi parmi H, C₁-C₆ alkyle, C₁-C₆ fluoroalkyle, et -OR12 ; R9 est choisi parmi H -NR13C(O)R14 et -C(O)NRlORl 1 ; R12 est choisi parmi H, C₁-C₆ alkyle et C₃-C₆ cycloalkyle, pour une utilisation comme inhibiteurs de l'enzyme DPP-IV dans le traitement ou la prévention de maladies comprenant le diabète de Type II.
• Deglycobleomycin A6 analogues modified in the methylvalerate moiety
  作者：Xiaoqing Cai、Paul A. Zaleski、Ali Cagir、Sidney M. Hecht

  DOI：10.1016/j.bmc.2011.04.047

  日期：2011.6

  Previous studies have indicated that the methylvalerate subunit of bleomycin (BLM) plays an important role in facilitating DNA cleavage by BLM and deglycoBLM. Eleven methylvalerate analogues have been synthesized and incorporated into deglycoBLM congeners by the use of solid-phase synthesis. The effect of the valerate moiety in the deglycoBLM analogues has been studied by comparison with the parent deglycoBLM A(5) using supercoiled DNA relaxation and sequence-selective DNA cleavage assays. All of the deglycoBLM analogues were found to effect the relaxation of the plasmid DNA. Those analogues having aromatic C4-substituents exhibited cleavage efficiency comparable to that of deglycoBLM A(5). Some, but not all, of the deglycoBLM analogues were also capable of mediating sequence-selective DNA cleavage. (C) 2011 Published by Elsevier Ltd.