2-O-methyl-4-nerolidylcatechol | 1160840-17-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-O-methyl-4-nerolidylcatechol
• 英文别名: 2-methoxy-4-(3,7,11-trimethyldodeca-1,6,10-trien-3-yl)phenol
• CAS: 1160840-17-4
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: CIIVLHVMOYVVOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-nerolidylcatechol 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 1-O-methyl-4-nerolidylcatechol 、 2-O-methyl-4-nerolidylcatechol
  参考文献：
  名称：

  New antimalarial and cytotoxic 4-nerolidylcatechol derivatives

  摘要：

  4-Nerolidylcatechol (1) was isolated from cultivated Pothomorphe peltata root on a multigram scale using straight-forward solvent extraction-column chromatography. New semi-synthetic derivatives of I were prepared and tested in vitro against multidrug-resistant Plasmodium falciparum K1 strain. Mono-O-methyl, mono-O-benzyl, O,O-dibenzyl and O,O-dibenzoyl derivatives 2-8 exhibited IC50 in the 0.67-22.52 mu M range. Mono-O-methyl ethers 6 and 7 inhibited the in vitro growth of human tumor cell lines HCT-8 (colon carcinoma), SF-295 (central nervous system), LH-60 (human myeloblastic leukemia) and MDA/MB-435 (melanoma). in general, derivatives 2-8 are more stable to light, air and pH at ambient temperatures than their labile, natural precursor 1. These derivatives provide leads for the development of a novel class of antimalarial drugs with enhanced chemical and pharmacological properties. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.025

文献信息

• [EN] DERIVATIVES OF 4-NEROLIDYLCATECHOL, PHARMACEUTICAL COMPOSITIONS COMPRISING THEM AND PROCESS FOR PRODUCING THE SAME<br/>[FR] DÉRIVÉS DE 4-NÉROLIDYLCATÉCHOL, COMPOSITIONS PHARMACEUTIQUES COMPRENANT CES DÉRIVÉS ET PROCÉDÉ DE PRÉPARATION DE CEUX-CI
  申请人：INST NAC DE PESQUISA DA AMAZON

  公开号：WO2009082795A1

  公开（公告）日：2009-07-09

  The present invention discloses 4-nerolidylcatechol and its derivatives isolated from South American / Amazon plants (Pothomorphe species) and their potential use as therapeutical agent for treatment of malarial symptoms, including malarial patients resistant to traditional drugs. The present invention also discloses a method for producing 4-nerolidylcatechol and their derivatives.

  本发明公开了从南美/亚马逊植物（Pothomorphe物种）中分离出的4-nerolidylcatechol及其衍生物，以及它们作为治疗疟疾症状的治疗剂的潜在用途，包括对传统药物具有抗药性的疟疾患者。本发明还公开了一种生产4-nerolidylcatechol及其衍生物的方法。