7-aminoheptanoic acid benzyl ester | 64054-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-aminoheptanoic acid benzyl ester
• 英文别名: Gln-OMe；7-amino-heptanoic acid benzyl ester；Benzyl 7-Aminoheptanoate；7-Aminoheptansaeurebenzylester
• CAS: 64054-48-4
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: IGIUOXOEWODHNE-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±25.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  7-aminoheptanoic acid benzyl ester 在 ammonium molybdate 双氧水 作用下， 以 甲醇 为溶剂， 反应 64.0h， 生成 7-{2-[3-benzyloxy-4-(4-fluoro-phenoxy)-butyl]-1,1,4-trioxo-1λ⁶-thiazolidin-3-yl}-heptanoic acid benzyl ester
  参考文献：
  名称：

  Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives

  摘要：

  A series of novel (8-aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids has been synthesized and evaluated for their ability to mimic the E series prostaglandins in stimulating cAMP formation in the mouse ovary and in binding to the rat kidney plasma prostaglandin receptor. 7-[2-(3-Hydroxyoctyl)-1,1,4-trioxo-3-thiazolidinyl]heptanoic acid markedly stimulates cAMP formation at reasonable pharmacological concentrations and avidly binds to the rat kidney prostaglandin receptor.

  DOI：

  10.1021/jm00220a013
• 作为产物：
  描述：

  7-氨基庚酸 在 氯化亚砜 作用下， 以 乙醇 、 苯甲醇 为溶剂， 生成 7-aminoheptanoic acid benzyl ester
  参考文献：
  名称：

  Certain thiazolidine compounds

  摘要：

  该发明涉及新型的8-氮杂-9-酮-11-硫代、-11-酮硫代和-11-二酮硫代前列腺酸化合物，其盐和衍生物，以及制备这些化合物的方法。这些化合物具有类似前列腺素的生物活性，特别适用于肾脏血管扩张剂，治疗某些自身免疫性疾病，并预防血栓形成。

  公开号：

  US04059587A1

文献信息

• Polypeptide conjugates with extended circulating half-lives
  申请人：——

  公开号：US20040254119A1

  公开（公告）日：2004-12-16

  The present invention relates to compounds and methods for synthesizing compounds wherein the compounds exhibit extended circulating half-life in the blood. The increase in circulating half-life is achieved by conjugating polypeptides to binding groups that exhibit high affinity for human serum albumin.

  本发明涉及化合物和合成化合物的方法，其中所述化合物在血液中表现出延长的循环半衰期。通过将多肽与具有高亲和力的结合基团偶联，实现循环半衰期的增加。该结合基团对人血清白蛋白具有高亲和力。
• Synthesis of betulinic acid derivatives as entry inhibitors against HIV-1 and bevirimat-resistant HIV-1 variants
  作者：Zhao Dang、Keduo Qian、Phong Ho、Lei Zhu、Kuo-Hsiung Lee、Li Huang、Chin-Ho Chen

  DOI：10.1016/j.bmcl.2012.06.080

  日期：2012.8

  Betulinic acid derivatives modified at the C28 position are HIV-1entry inhibitors such as compound A43D; however, modified at the C3 position instead of C28 give HIV-1 maturation inhibitor such as bevirimat. Bevirimat exhibited promising pharmacokinetic profiles in clinical trials, but its effectiveness was compromised by the high baseline drug resistance of HIV-1 variants with polymorphism in the putative drug binding site. In an effort to determine whether the viruses with bevirimat resistant polymorphism also altered their sensitivities to the betulinic acid derivatives that inhibit HIV-1 entry, a series of new betulinic acid entry inhibitors were synthesized and tested for their activities against HIV-1 NL4-3 and NL4-3 variants resistant to bevirimat. The results show that the bevirimat resistant viruses were approximately 5- to10-fold more sensitive to three new glutamine ester derivatives (13, 15 and 38) and A43D in an HIV-1 multi-cycle replication assay. In contrast, the wild type NL4-3 and the bevirimat resistant variants were equally sensitive to the HIV-1 RT inhibitor AZT. In addition, these three new compounds markedly improved microsomal stability compared to A43D. (c) 2012 Elsevier Ltd. All rights reserved.
• 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.
• Design and synthesis of novel and highly-active pan-histone deacetylase (pan-HDAC) inhibitors
  作者：Toshihiko Tashima、Hiroaki Murata、Hidehiko Kodama

  DOI：10.1016/j.bmc.2014.05.001

  日期：2014.7

  Histone deacetylase (HDAC) inhibitions are known to elicit anticancer effects. We designed and synthesized several HDAC inhibitors. Among these compounds, compound 40 exhibited a more than 10-fold stronger inhibitory activity compared with that of suberoylanilide hydroxamic acid (SAHA) against each human HDAC isozyme in vitro (IC50 values of 40: HDAC1, 0.0038μM; HDAC2, 0.0082μM; HDAC3, 0.015μM; HDAC8, 0.0060μM; HDAC4, 0.058μM; HDAC9, 0.0052μM; HDAC6, 0.058μM). The dose of the administered HDAC inhibitors that contain hydroxamic acid as the zinc-binding group may be reduced by 40. Because the carbostyril subunit is a time-tested structural component of drugs and biologically active compounds, 40 most likely exhibits good absorption, distribution, metabolism, excretion, and toxicity (ADMET). Thus, compound 40 is expected to be a promising therapeutic agent or chemical tool for the investigation of life process.
• Betulinic Acid Derivatives as Human Immunodeficiency Virus Type 2 (HIV-2) Inhibitors
  作者：Zhao Dang、Weihong Lai、Keduo Qian、Phong Ho、Kuo-Hsiung Lee、Chin-Ho Chen、Li Huang

  DOI：10.1021/jm9004253

  日期：2009.12.10

  We previously reported that [[N-[3 beta-hydroxyllup-20(29)-en-28-oyl]-7-aminoheptyl]carbamoyl]methane (A43D, 4) was a potent HIV-1 entry inhibitor. However, 4 was inactive against HIV-2 virus, suggesting the structural requirements for targeting these two retroviruses are different. In this study, a series of new betulinic acid derivatives were synthesized, and some of them displayed selective anti-HIV-2 activity at nanomolar concentrations. In comparison to compounds with anti-HIV-1 activity, a shorter C-28 side chain is required for optimal anti-HIV-2 activity.