(butanoyloxy)methyl octanoate | 138460-00-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (butanoyloxy)methyl octanoate
• 英文别名: (butyroyloxy)methyl octanoate；(butyroxy)methyl octanoate；Butanoyloxymethyl octanoate
• CAS: 138460-00-1
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: POSXGLRSYWUWNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  辛酸 在 四丁基硫酸氢铵 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 生成 (butanoyloxy)methyl octanoate
  参考文献：
  名称：

  Novel anticancer prodrugs of butyric acid. 2

  摘要：

  The antitumor activity of novel prodrugs butyric acid was examined. The in vitro effect of the compounds on induction of cytodifferentiation and on inhibition of proliferation and clonogenicity showed that (pivaloyloxy)methyl butyrate (1a) (labeled AN-9) was the most active agent. SAR's suggested that its activity stemmed from hydrolytically released butyric acid. In vivo, 1a displayed antitumor activity in B16F0 melanoma primary cancer model, manifested by a significant increase in the life span of the treated animals. Murine lung tumor burden, induced by injection of the highly metastatic melanoma cells (B16F10.9), was decreased by 1a. It also displayed a significant therapeutic activity against spontaneous metastases which were induced by 3LL Lewis lung carcinoma cells. Moreover, 1a has the advantage of low toxicity, with an acute LD50 = 1.36 +/- 0.1 g/kg (n = 5). These results suggest that 1a is a potential antineoplastic agent.

  DOI：

  10.1021/jm00082a009

文献信息

• EP0793488A4
  申请人：——

  公开号：EP0793488A4

  公开（公告）日：1997-09-10
• INCREASING FETAL HEMOGLOBIN LEVELS USING CARBOXYLIC ESTERS
  申请人：Rephaeli, Ada

  公开号：EP0793488A1

  公开（公告）日：1997-09-10
• US5569675A
  申请人：——

  公开号：US5569675A

  公开（公告）日：1996-10-29
• US5962523A
  申请人：——

  公开号：US5962523A

  公开（公告）日：1999-10-05
• [EN] INCREASING FETAL HEMOGLOBIN LEVELS USING CARBOXYLIC ESTERS<br/>[FR] ACCROISSEMENT DU TAUX D'HEMOGLOBINE FOETALE AU MOYEN D'ESTERS CARBOXYLIQUES
  申请人：REPHAELI, Ada

  公开号：WO1995024189A1

  公开（公告）日：1995-09-14

  (EN) This invention relates to novel methods of increasing the level of fetal hemoglobin (HbF) in a subject and methods of treating, preventing or ameliorating $g(b)-globin or other HbF-related disorders by increasing the level of HbF in a subject in need of such treatment comprising administering one or more compounds of the formulae: (I) XCH2-CHX-CHX-C(=O)-O-Z, (II) CH3-CO-CH2-C(=O)-O-Z or (III) CH3-CH2-CO-C(=O)-O-Z, wherein X is H, or one of X only may be OH; Z is -CHR-O-C(=O)R', -CHR-O-C(=O)-O-R', or (IV); R is H, alkyl, aryl, arylalkyl; and R' is alkyl, aminoalkyl, aralkyl, aryl, alkoxy, aralkoxy and aryloxy, in which aryl by itself, and aryl in aralkyl, aralkoxy and aryloxy are each selected from the group consisting of phenyl, naphthyl, furyl, or thienyl, each of which is unsubstituted or substituted by at least one substituent selected from the group consisting of alkyl, alkoxy, or halogen; and pharmaceutically acceptable salts and prodrugs thereof.(FR) La présente invention concerne de nouveaux procédés permettant d'accroître le taux d'hémoglobine f÷tale (HbF) d'un sujet ainsi que des procédés de traitement, de prévention ou d'amélioration de la $g(b)-globine ou d'autres troubles imputables à la HbF en accroissant le taux de HbF chez un sujet nécessitant un tel traitement, consistant en l'administration d'un ou plusieurs composés des formules (I) XCH2-CHX-CHX-C(=O)-O-Z, (II) CH3-CO-CH2-C(=O)-O-Z ou (III) CH3-CH2-CO-C(=O)-O-Z ou de l'un de ses sels pharmaceutiquement acceptables ou l'un de ses précurseurs médicamenteux. Dans ces formules, X est H, mais l'un des X peut être OH; Z est -CHR-O-C(=O)R', -CHR-O-C(=O)-O-R' ou être représenté par le schéma (IV); R est un H, alkyle, aryle, arylalkyle et R' est un alkyle, aminoalkyle, aralkyle, aryle, alcoxy, aralcoxy et aryloxy. Dans ce dernier radical, l'aryle en tant que tel, l'aryle d'aralkyle, l'aralcoxy et l'aryloxy appartiennent chacun à un groupe formé de phényle, naphtyle, furyle ou thiényle, chacun d'entre eux pouvant être non substitué ou substitué par l'un au moins des substituants appartenant au groupe formé d'alkyle, alcoxy ou halogène.