(R)-2-Amino-4,4-dimethoxy-2-naphthalen-1-ylmethyl-butyric acid methyl ester | 847020-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-Amino-4,4-dimethoxy-2-naphthalen-1-ylmethyl-butyric acid methyl ester
• 英文别名: methyl (2R)-2-amino-4,4-dimethoxy-2-(naphthalen-1-ylmethyl)butanoate
• CAS: 847020-71-7
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: WZDNBSKQEDAFAS-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-4,4-dimethoxy-2-naphthalen-1-ylmethyl-butyric acid methyl ester 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 5.0h， 生成 (2R,5'S,5''R)-5'-(4-Azido-butyl)-4-benzyl-5''-(2,2-dimethoxy-ethyl)-2-isopropyl-5''-naphthalen-1-ylmethyl-1,2,1',2',1'',5''-hexahydro-[2,3';5',3'']terpyrrole-3,4',4''-trione
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  1-溴甲基萘 在 palladium on activated charcoal 氢氧化钾 、 四氧化锇 、 四(三苯基膦)钯 、 氢气 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 13.5h， 生成 (R)-2-Amino-4,4-dimethoxy-2-naphthalen-1-ylmethyl-butyric acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974

文献信息

• Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics
  作者：Amos B. Smith、Adam K. Charnley、Eugen F. Mesaros、Osamu Kikuchi、Wenyong Wang、Andrew Benowitz、Chi-Lien Chu、Jin-Jye Feng、Kuo-Hsin Chen、Atsui Lin、Fong-Chi Cheng、Laurie Taylor、Ralph Hirschmann

  DOI：10.1021/ol0476974

  日期：2005.2.1

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.