(S)-1-(3-(hydroxymethyl)phenyl)octyl acetate | 1372526-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (S)-1-(3-(hydroxymethyl)phenyl)octyl acetate
• 英文别名: [(1S)-1-[3-(hydroxymethyl)phenyl]octyl] acetate
• CAS: 1372526-62-9
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: KZTLTVABFNHKTH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-(hydroxymethyl)phenyl)octyl acetate 在 草酰氯 、 三乙酰氧基硼氢化钠 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-(4-chlorophenyl)(3-((1-(3-(1-hydroxyoctyl)benzyl)piperidin-4-yl)methoxy)phenyl) methanone
  参考文献：
  名称：

  Discovery of Selective Menaquinone Biosynthesis Inhibitors against Mycobacterium tuberculosis

  摘要：

  Aurachin RE (1) is a strong antibiotic that was recently found to possess 1,4-dihydroxy-2-naphthoate prenyltransferase (MenA) and bacterial electron transport inhibitory activities. Aurachin RE is the only molecule in a series of aurachin natural products that has the chiral center in the alkyl side chain at C9'-position. To identify selective MenA inhibitors against Mycobacterium tuberculosis, a series of chiral molecules were designed based on the structures of previously identified MenA inhibitors and 1. The synthesized molecules were evaluated in in vitro assays, including MenA enzyme and bacterial growth inhibitory assays. We could identify novel MenA inhibitors that showed significant increase in potency of killing nonreplicating M. tuberculosis in the low oxygen recovery assay (LORA) without inhibiting other Gram-positive bacterial growth even at high concentrations. The MenA inhibitors reported here are useful new pharmacophores for the development of selective antimycobacterial agents with strong activity against nonreplicating M. tuberculosis.

  DOI：

  10.1021/jm201608g
• 作为产物：
  描述：

  N-甲氧基-N-甲基辛酰胺 在 吡啶 、 四丁基氟化铵 、 异丙基氯化镁 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 (S)-1-(3-(hydroxymethyl)phenyl)octyl acetate
  参考文献：
  名称：

  Discovery of Selective Menaquinone Biosynthesis Inhibitors against Mycobacterium tuberculosis

  摘要：

  Aurachin RE (1) is a strong antibiotic that was recently found to possess 1,4-dihydroxy-2-naphthoate prenyltransferase (MenA) and bacterial electron transport inhibitory activities. Aurachin RE is the only molecule in a series of aurachin natural products that has the chiral center in the alkyl side chain at C9'-position. To identify selective MenA inhibitors against Mycobacterium tuberculosis, a series of chiral molecules were designed based on the structures of previously identified MenA inhibitors and 1. The synthesized molecules were evaluated in in vitro assays, including MenA enzyme and bacterial growth inhibitory assays. We could identify novel MenA inhibitors that showed significant increase in potency of killing nonreplicating M. tuberculosis in the low oxygen recovery assay (LORA) without inhibiting other Gram-positive bacterial growth even at high concentrations. The MenA inhibitors reported here are useful new pharmacophores for the development of selective antimycobacterial agents with strong activity against nonreplicating M. tuberculosis.

  DOI：

  10.1021/jm201608g

文献信息

• [EN] COMPOSITIONS FOR THE TREATMENT OF TUBERCULOSIS AND METHODS OF USING SAME<br/>[FR] COMPOSITIONS POUR LE TRAITEMENT DE LA TUBERCULOSE ET PROCÉDÉS D'UTILISATION DE CELLES-CI
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2013116605A1

  公开（公告）日：2013-08-08

  The present application relates to therapeutic compounds, compositions comprising an effective amount of a therapeutic compound; and methods for treating and preventing tuberculosis comprising administering and effective amount of a therapeutic compound to a subject in need thereof.