isopropyl L-2-aminobutyrate | 56194-11-7

• 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: isopropyl L-2-aminobutyrate
• 英文别名: (S)-isopropyl 2-aminobutyrate；(S)-isopropyl 2-aminobutanoate；propan-2-yl (2S)-2-aminobutanoate
• CAS: 56194-11-7
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: ZJIVVFUSMATLTN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  isopropyl L-2-aminobutyrate 、 二氯磷酸苯酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Nucleotide Prodrugs of 2′-Deoxy-2′-spirooxetane Ribonucleosides as Novel Inhibitors of the HCV NS5B Polymerase

  摘要：

  The limited efficacy, in particular against the genotype 1 virus, as well as the variety of side effects associated with the current therapy for hepatitis C virus (HCV) infection necessitates more efficacious drugs. We found that phosphoramidate prodrugs of 2'-deoxy-2'-spirooxetane ribonucleosides form a novel class of HCV NS5B RNA-dependent RNA polymerase inhibitors, displaying EC50 values ranging from 0.2 to >98 mu M, measured in the Huh7-replicon cell line, with no apparent cytotoxicity (CC50 > 98.4 mu M). Confirming recent findings, the 2'-spirooxetane moiety was identified as a novel structural motif in the field of anti-HCV nucleosides. A convenient synthesis was developed that enabled the synthesis of a broad set of nucleotide prodrugs with varying substitution patterns. Extensive formation of the triphosphate metabolite was observed in both rat and human hepatocyte cultures. In addition, after oral dosing of several phosphoramidate derivatives of compound 21 to rats, substantial hepatic levels of the active triphosphate metabolite were found.

  DOI：

  10.1021/jm4015422
• 作为产物：
  描述：

  α-Keto-buttersaeure-isopropylester 在 磷酸吡哆醛 、 Prozomix amine transaminase 230 、 异丙胺 作用下， 以 aq. phosphate buffer 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  WO2023/197017

  摘要：

  公开号：

文献信息

• 一种新型替诺福韦混合酯-酰胺前药
  申请人：正大天晴药业集团股份有限公司

  公开号：CN110938095A

  公开（公告）日：2020-03-31

  本申请涉及一种新型替诺福韦混合酯‑酰胺前药或其药学上可接受的盐、其制备方法、含有这些前药化合物的药物组合物，及其在制备用于治疗病毒感染例如乙型肝炎病毒(HBV)或人类免疫缺陷病毒(HIV)感染的药物的用途。
• PRODRUGS OF PHOSPHONATE NUCLEOTIDE ANALOGUES
  申请人：Becker Mark W.

  公开号：US20080227754A1

  公开（公告）日：2008-09-18

  A novel method has led to the identification of novel mixed ester-amidates of PMPA for retroviral or hepadnaviral therapy, including compounds of structure (5a) having substituent groups as defined herein. Compositions of these novel compounds in pharmaceutically acceptable excipients and their use in therapy and prophylaxis are provided.

  一种新的方法导致了PMPA的新型混合酯酰胺化合物的识别，用于逆转录病毒或乙肝病毒治疗，其中包括具有如下所定义的取代基团的结构（5a）化合物。提供这些新型化合物在药学上可接受的载体中的组成物以及它们在治疗和预防中的使用。
• 2'-Ethynyl Nucleoside Derivatives for Treatment of Viral Infections
  申请人：ANADAN Sampath-Kumar

  公开号：US20150232501A1

  公开（公告）日：2015-08-20

  The present invention provides a compound of formula A: or a pharmaceutically acceptable salt thereof, wherein B, Q, R 1 , R 5 , R 6 , R 7 , R 8 and Z are as defined herein, which is a 2′-branched nucleoside useful for the treatment or prevention of viral infections, particularly dengue fever, yellow fever, West Nile virus, Japanese encephalitis virus, tick-borne encephalitis virus, Kunjin virus, Murray Valley encephalitis, St Louis encephalitis, Omsk hemorrhagic fever virus, bovine viral diarrhea virus, Zika virus and Hepatitis C virus.

  本发明提供了化合物A的公式：或其药学上可接受的盐，其中B、Q、R1、R5、R6、R7、R8和Z的定义如本文所述，该化合物是一种2'-支链核苷酸，可用于治疗或预防病毒感染，特别是登革热、黄热病、西尼罗河病毒、日本脑炎病毒、蜱媒脑炎病毒、昆津病毒、默里谷脑炎、圣路易斯脑炎、鄂木斯克出血热病毒、牛病毒性腹泻病毒、寨卡病毒和丙型肝炎病毒。
• PRODRUGS OF PHOSPHONATE NUCLEOTIDE ANALOGUES AND METHODS FOR SELECTING AND MAKING SAME
  申请人：GILEAD SCIENCES, INC.

  公开号：EP1301519B2

  公开（公告）日：2021-11-10
• Prodrugs of phosphonate nucleotide analogues and methods for selecting and making same
  申请人：GILEAD SCIENCES, INC.

  公开号：EP2682397B1

  公开（公告）日：2017-04-19