3,5-dimethoxy-4-[[N-(n-butyl)amino]carbonyl]benzaldehyde | 380922-35-0

• 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: 3,5-dimethoxy-4-[[N-(n-butyl)amino]carbonyl]benzaldehyde
• 英文别名: N-butyl-4-formyl-2,6-dimethoxybenzamide
• CAS: 380922-35-0
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: ZAQFLVCKKLLCBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-4-[[N-(n-butyl)amino]carbonyl]benzaldehyde 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 125.0 ℃ 、101.33 kPa 条件下， 反应 2.33h， 生成 4-[3-Acetyl-5-(4-amino-3-methyl-phenyl)-2,3-dihydro-[1,3,4]oxadiazol-2-yl]-N-butyl-2,6-dimethoxy-benzamide
  参考文献：
  名称：

  New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models

  摘要：

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.

  DOI：

  10.1021/jm010231w
• 作为产物：
  描述：

  4-(hydroxymethyl)-2,6-dimethoxybenzoic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3,5-dimethoxy-4-[[N-(n-butyl)amino]carbonyl]benzaldehyde
  参考文献：
  名称：

  New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models

  摘要：

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.

  DOI：

  10.1021/jm010231w

文献信息

• New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models
  作者：Bruce G. Szczepankiewicz、Gang Liu、Hwan-Soo Jae、Andrew S. Tasker、Indrani W. Gunawardana、Thomas W. von Geldern、Stephen L. Gwaltney、J. Ruth Wu-Wong、Laura Gehrke、William J. Chiou、R. Bruce Credo、Jeffery D. Alder、Michael A. Nukkala、Nicolette A. Zielinski、Ken Jarvis、Karl W. Mollison、David J. Frost、Joy L. Bauch、Yu Hua Hui、Akiyo K. Claiborne、Qun Li、Saul H. Rosenberg

  DOI：10.1021/jm010231w

  日期：2001.12.1

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.