(S)-(1,5-二氨基-1,5-二氧代-2-戊基)氨基甲酸叔丁酯 | 77345-20-1

• 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
• 中文名称: (S)-(1,5-二氨基-1,5-二氧代-2-戊基)氨基甲酸叔丁酯
• 英文名称: (S)-N-α-tert-butoxycarbonylglutamineamide
• 英文别名: Boc-Gln-NH2；Boc-glutamine；(2S)-2-tert-butoxycarbonylaminopentanedioic acid diamide；(S)-tert-Butyl (1,5-diamino-1,5-dioxopentan-2-yl)carbamate；tert-butyl N-[(2S)-1,5-diamino-1,5-dioxopentan-2-yl]carbamate
• CAS: 77345-20-1
• 化学式: C₁₀H₁₉N₃O₄
• 分子量: 245.279
• InChiKey: PBSXSUBRKKDHPQ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  (S)-(1,5-二氨基-1,5-二氧代-2-戊基)氨基甲酸叔丁酯 在 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 反应 0.75h， 生成 L-glutamic acid diamide
  参考文献：
  名称：

  Structure activity studies on the C-terminal hexapeptide of substance P with modifications at the glutaminyl and methioninyl residues

  摘要：

  Analogues of [Orn6]-SP6-11 have been synthesized in which the SCH3 group of the Met11 side chain is replaced by other functional groups, such as (CH2)2NH2, COOH, CONH2, and COOR, which have basic, acid, or neutral character and which may act as either H-bonding donors or H-bonding acceptors. These analogues were tested in guinea pig ileum and rat colon muscularis mucosae, in vitro. Substitution of Lys, Gln, or Glu at position 11 caused a marked reduction in biological activity in both tissues. In contrast, the glutamate benzyl ester analogue had only slightly reduced activity in the guinea pig ileum and an increased (4.7 times) activity in the rat colon. It is concluded that charged groups in the side chain at position 11 of SP6-11 reduce the biological activity of SP hexapeptide.

  DOI：

  10.1021/jm00391a041
• 作为产物：
  描述：

  Boc-L-谷氨酰胺 在 N-甲基吗啉 、 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.53h， 生成 (S)-(1,5-二氨基-1,5-二氧代-2-戊基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Structure activity studies on the C-terminal hexapeptide of substance P with modifications at the glutaminyl and methioninyl residues

  摘要：

  Analogues of [Orn6]-SP6-11 have been synthesized in which the SCH3 group of the Met11 side chain is replaced by other functional groups, such as (CH2)2NH2, COOH, CONH2, and COOR, which have basic, acid, or neutral character and which may act as either H-bonding donors or H-bonding acceptors. These analogues were tested in guinea pig ileum and rat colon muscularis mucosae, in vitro. Substitution of Lys, Gln, or Glu at position 11 caused a marked reduction in biological activity in both tissues. In contrast, the glutamate benzyl ester analogue had only slightly reduced activity in the guinea pig ileum and an increased (4.7 times) activity in the rat colon. It is concluded that charged groups in the side chain at position 11 of SP6-11 reduce the biological activity of SP hexapeptide.

  DOI：

  10.1021/jm00391a041

文献信息

• STEREOSELECTIVE SYNTHESIS OF PIPERIDINE DERIVATIVES
  申请人：Chou Shan-Yen

  公开号：US20100152452A1

  公开（公告）日：2010-06-17

  This invention relates to dialdehyde or dinitrile compounds, which are useful for stereoselective synthesis of piperidine, pyrrolidine, and azepane derivatives.

  这项发明涉及二醛或二腈化合物，可用于对哌啶、吡咯烷和氮杂环庚烷衍生物进行立体选择性合成。
• New Betulinic Acid Derivatives for Bevirimat-Resistant Human Immunodeficiency Virus Type-1
  作者：Zhao Dang、Phong Ho、Lei Zhu、Keduo Qian、Kuo-Hsiung Lee、Li Huang、Chin-Ho Chen

  DOI：10.1021/jm3016969

  日期：2013.3.14

  Bevirimat (1, BVM) is an anti-HIV agent that blocks HIV-1 replication by interfering with HIV-1 Gag-SP1 processing at a late stage of viral maturation. However, clinical trials of 1 have revealed a high baseline drug resistance that is attributed to naturally occurring polymorphisms in HIV-1 Gag. To overcome the drug resistance, 28 new derivatives of 1 were synthesized and tested against compound 1-resistant (BVM-R) HIV-1 variants. Among them, compound 6 exhibited much improved activity against several HIV-1 strains carrying BVM-R polymorphisms. Compound 6 was at least 20-fold more potent than 1 against the replication of NL4-3/V370A, which carries the most prevalent clinical BVM-R polymorphism in HIV-1 Gag-SP1. Thus, compound 6 merits further development as a potential anti-AIDS clinical trial candidate.
• POULOS, C.;STAVROPOULOS, G.;BROWN, J. R.;JORDAN, CH. C., J. MED. CHEM., 30,(1987) N 8, 1512-1515
  作者：POULOS, C.、STAVROPOULOS, G.、BROWN, J. R.、JORDAN, CH. C.

  DOI：——

  日期：——
• [EN] STEREOSELECTIVE SYNTHESIS OF PIPERIDINE DERIVATIVES<br/>[FR] SYNTHÈSE STÉRÉOSÉLECTIVE DE DÉRIVÉS DE PIPÉRIDINE
  申请人：TAIGEN BIOTECHNOLOGY CO LTD

  公开号：WO2010077798A2

  公开（公告）日：2010-07-08

  This invention relates to dialdehyde or dinitrile compounds, which are useful for stereoselective synthesis of piperidine, pyrrolidine, and azepane derivatives.
• Design, Synthesis, and Preliminary Pharmacological Evaluation of <i>N</i>-Acyl-3-aminoglutarimides as Broad-Spectrum Chemokine Inhibitors in Vitro and Anti-inflammatory Agents in Vivo
  作者：David J. Fox、Jill Reckless、Stuart G. Warren、David J. Grainger

  DOI：10.1021/jm010984i

  日期：2002.1.1

  A series of N-substituted 3-aminoglutarimides have been synthesized and tested for inhibitory activity against a range of chemokines in vitro and for suppression of lipopolysaccharide-induced inflammation in vivo. The results show that they represent the first class of small molecules with broad-spectrum chemokine inhibitory effects. Among the compounds studied, 10 (NR58,4) was the most potent, being active at doses between 5 and 15 nM in vitro and at 0.3 mg kg(-1) in vivo.