(R)-2-methyl-4-aminononane hydrochloride | 129603-18-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-2-methyl-4-aminononane hydrochloride
• 英文别名: (4R)-2-methylnonan-4-amine;hydrochloride
• CAS: 129603-18-5
• 化学式: C₁₀H₂₃N*ClH
• 分子量: 193.76
• InChiKey: IBCYZQYZUSPYJM-HNCPQSOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-4-aminononane hydrochloride 在 N-甲基吗啉 、 盐酸 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 20.25h， 生成 (R)-2-methyl-4-nonanyl-(S)-histidinamide dihydrochloride
  参考文献：
  名称：

  Gastrin releasing peptide antagonists with improved potency and stability

  摘要：

  Gastrin releasing peptide (GRP) is a 27 amino acid peptide hormone which is homologous to the amphibian peptide bombesin. Two series of novel GRP antagonists were developed by C-terminal modification of N-acetyl-GRP-20-27 amide. Peptide derivatives within each series resist enzymatic degradation in serum and exhibit strong affinity for the GRP receptor. The first series of compounds replaces the Leu26-Met27 region of GRP with an alkyl ether moiety. One member of this series, N-acetyl-GRP-20-25-NH-[(S)-1-ethoxy-4-methyl-2-pentane], specifically blocked radiolabeled GRP binding with an IC50 of 6 nM. In the second series of antagonists the oxygen of the ether moiety is replaced with a methylene group, resulting in GRP antagonists which are equipotent to native GRP in receptor binding assays (IC50 = 2 nM) and are also resistant to proteolytic degradation in vitro. All of the C-terminally modified peptides tested blocked GRP-stimulated mitogenesis in Swiss 3T3 mouse fibroblasts. Representative compounds also blocked GRP-induced elevation of [Ca2+]i in human SCLC cells, and inhibited GRP-independent release of gastrin in vivo.

  DOI：

  10.1021/jm00111a027
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-4-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 盐酸 、 palladium on activated charcoal 、 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、262.01 kPa 条件下， 生成 (R)-2-methyl-4-aminononane hydrochloride
  参考文献：
  名称：

  A Convenient and Versatile Synthesis of Chiral Aliphatic and Allylic Amines

  摘要：

  本文描述了从氨基酸制备光学纯脂肪族和烯丙基胺的方法。通过Wittig烯烃化反应，将α-Boc-氨基酸醛转化为Boc保护的烯丙基胺，再脱保护得到相应的手性不饱和胺。在脱保护之前对Wittig产物进行催化还原，可以获得高光学纯度的脂肪族胺。

  DOI：

  10.1055/s-1990-26900

文献信息

• A Convenient and Versatile Synthesis of Chiral Aliphatic and Allylic Amines
  作者：Walfred S. Saari、Thorsten E. Fisher

  DOI：10.1055/s-1990-26900

  日期：——

  Preparation of optically pure aliphatic and allylic amines from amino acids is described. Wittig olefination of α-Boc-amino aldehydes affords Boc-protected allylic amines which can be deprotected to the corresponding chiral unsaturated amines. Catalytic reduction of the Wittig product prior to deprotection affords aliphatic amines of high optical purity.

  本文描述了从氨基酸制备光学纯脂肪族和烯丙基胺的方法。通过Wittig烯烃化反应，将α-Boc-氨基酸醛转化为Boc保护的烯丙基胺，再脱保护得到相应的手性不饱和胺。在脱保护之前对Wittig产物进行催化还原，可以获得高光学纯度的脂肪族胺。
• Gastrin releasing peptide antagonists
  申请人：Merck & Co., Inc.

  公开号：EP0371543A2

  公开（公告）日：1990-06-06

  Small cell lung carcinoma (SCLC) cells contain gastrin releasing peptide (GRP) receptors. The response of the cells to GRP is rapid growth. We have found a group of peptide derivatives that act as GRP antagonists by blocking the binding of GRP to its receptor thereby inhibiting the growth of cells that are sensitive to the growth promoting activity of GRP.

  小细胞肺癌（SCLC）细胞含有胃泌素释放肽（GRP）受体。细胞对 GRP 的反应是快速生长。我们发现一组肽衍生物可作为 GRP 拮抗剂，通过阻断 GRP 与其受体的结合，从而抑制对 GRP 促进生长活性敏感的细胞的生长。
• SAARI, WALFRED S.;FISHER, THORSTEN E., LAB. MICROCOMPUT., 9,(1990) N, C. 453-454
  作者：SAARI, WALFRED S.、FISHER, THORSTEN E.

  DOI：——

  日期：——
• HEIMBROOK, DAVID C.;REIMEN, MARK W.;OLIFF, ALLEU;SAARI, WALFRED S.
  作者：HEIMBROOK, DAVID C.、REIMEN, MARK W.、OLIFF, ALLEU、SAARI, WALFRED S.

  DOI：——

  日期：——
• US4943561A
  申请人：——

  公开号：US4943561A

  公开（公告）日：1990-07-24