Trimethylsilyl 5-aminopentanoate | 53611-23-7

• 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: Trimethylsilyl 5-aminopentanoate
• 英文别名: trimethylsilyl 5-aminopentanoate
• CAS: 53611-23-7
• 化学式: C₈H₁₉NO₂Si
• 分子量: 189.33
• InChiKey: OMUQBVCUBCBMBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Trimethylsilyl 5-aminopentanoate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl 5-[5-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]amino]pentanoylamino]pentanoate
  参考文献：
  名称：

  Betulinic Acid Derivatives:  A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1 Entry

  摘要：

  A novel series of omega-aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). The anti-HIV-1 activity of several members of this new series was found to be in the nanomolar range in CEM 4 and MT-4 cell cultures. The optimization of the omega-aminoalkanoic acid side chain is described. The presence of an amide function within the side chain was found important for optimal activity. RPR 103611 (14g), a statine derivative, was found to be inactive against HIV-1 protease, reverse transcriptase, and integrase as well as on gp120/CD4 binding. ''Time of addition'' experiments suggested interaction with an early step of HIV-1 replication. As syncytium formation, but not virus-cell binding, seems to be affected, betulinic acid derivatives are assumed to interact with the postbinding virus-cell fusion process.

  DOI：

  10.1021/jm950669u
• 作为产物：
  描述：

  三甲基氯硅烷 、 5-氨基颉草酸 以 二氯甲烷 为溶剂， 生成 Trimethylsilyl 5-aminopentanoate
  参考文献：
  名称：

  从氨基酸实际合成游离和受保护的胍基酸

  摘要：

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。

  DOI：

  10.1016/0040-4039(96)00299-7

文献信息

• A practical synthesis of free and protected guanidino acids from amino acids
  作者：Bansi Lal、A.K. Gangopadhyay

  DOI：10.1016/0040-4039(96)00299-7

  日期：1996.4

  Synthesis of protected guanidino acids in one pot reaction is achieved. Amino acids are treated with trimethylsilyl chloride, triethylamine, dicarbobenzoxy-S-methyl isothiourea in dichloromethane followed by removal of silyl group by treatment with methanol to give the corresponding carbobenzoxy guanidino acids.

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。
• Betulinic Acid Derivatives:  A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1 Entry
  作者：Françoise Soler、Christèle Poujade、Michel Evers、Jean-Christophe Carry、Yvette Hénin、Anne Bousseau、Thierry Huet、Rudi Pauwels、Erik De Clercq、Jean-François Mayaux、Jean-Bernard Le Pecq、Norbert Dereu

  DOI：10.1021/jm950669u

  日期：1996.1.1

  A novel series of omega-aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). The anti-HIV-1 activity of several members of this new series was found to be in the nanomolar range in CEM 4 and MT-4 cell cultures. The optimization of the omega-aminoalkanoic acid side chain is described. The presence of an amide function within the side chain was found important for optimal activity. RPR 103611 (14g), a statine derivative, was found to be inactive against HIV-1 protease, reverse transcriptase, and integrase as well as on gp120/CD4 binding. ''Time of addition'' experiments suggested interaction with an early step of HIV-1 replication. As syncytium formation, but not virus-cell binding, seems to be affected, betulinic acid derivatives are assumed to interact with the postbinding virus-cell fusion process.
• Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin
  作者：Andrea Leone-Bay、Duncan R. Paton、John Freeman、Christine Lercara、Doris O'Toole、David Gschneidner、Eric Wang、Elizabeth Harris、Connie Rosado、Theresa Rivera、Aldonna DeVincent、Monica Tai、Frank Mercogliano、Rajesh Agarwal、Harry Leipold、Robert A. Baughman

  DOI：10.1021/jm970811m

  日期：1998.3.1

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.