2,3,N-trimethoxy-N-methylbenzamide | 205320-01-0

• 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: 2,3,N-trimethoxy-N-methylbenzamide
• 英文别名: N,2,3-trimethoxy-N-methylbenzamide
• CAS: 205320-01-0
• 化学式: C₁₁H₁₅NO₄
• mdl: MFCD18918939
• 分子量: 225.244
• InChiKey: CROLUNLNTXTMSD-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  382.8±32.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,N-trimethoxy-N-methylbenzamide 在 重铬酸吡啶 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 3-(2,3-dimethoxybenzoyl)benzaldehyde
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.83h， 生成 2,3,N-trimethoxy-N-methylbenzamide
  参考文献：
  名称：

  Synthesis of the α,β-Unsaturated δ-Lactones (+)-Anhydrocalopin and (+)-Dehydrocalopin

  摘要：

  在我们对蘑菇代谢物中刺孢组的研究过程中，我们开发了一种合成3,4-二取代α,β-不饱和δ-内酯的方法。该合成方法被应用于光学活性的脱氢假刺孢素（2）和无水假刺孢素（3）的合成。

  DOI：

  10.1055/s-2003-36269

文献信息

• ESTROGEN RECEPTOR MODULATORS AND USES THEREOF
  申请人：Genentech, Inc.

  公开号：US20160175284A1

  公开（公告）日：2016-06-23

  Described herein are compounds that are estrogen receptor modulators of Formula I: and stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, and with the substituents and structural features described herein. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

  本文描述的是一些具有公式I的雌激素受体调节剂，以及其立体异构体、互变异构体或药学上可接受的盐，以及所述的取代基和结构特征。还描述了包括上述化合物的药物组合物和药物，以及使用这些雌激素受体调节剂的方法，单独或与其他化合物结合，用于治疗介导或依赖于雌激素受体的疾病或症状。
• An Efficient and Versatile Synthesis of Isoflavones from 2-Methoxybenzoic Acids
  作者：Jae In Lee

  DOI：10.1002/bkcs.10806

  日期：2016.7
• Discovery of a C-8 hydroxychromene as a potent degrader of estrogen receptor alpha with improved rat oral exposure over GDC-0927
  作者：Sharada S. Labadie、Jun Li、Robert A. Blake、Jae H. Chang、Simon Goodacre、Steven J. Hartman、Weiling Liang、James R. Kiefer、Tracy Kleinheinz、Tommy Lai、Jiangpeng Liao、Daniel F. Ortwine、Vidhi Mody、Nicholas C. Ray、Fabien Roussel、Maia Vinogradova、Siew Kuen Yeap、Birong Zhang、Xiaoping Zheng、Jason R. Zbieg、Jun Liang、Xiaojing Wang

  DOI：10.1016/j.bmcl.2019.07.013

  日期：2019.8

  Phenolic groups are responsible for the high clearance and low oral bioavailability of the estrogen receptor alpha (ER alpha) clinical candidate GDC-0927. An exhaustive search for a backup molecule with improved pharmacokinetic (PK) properties identified several metabolically stable analogs, although in general at the expense of the desired potency and degradation efficiency. C-8 hydroxychromene 30 is the first example of a phenol-containing chromene that not only maintained excellent potency but also exhibited 10-fold higher oral exposure in rats. The improved in vivo clearance in rat was hypothesized to be the result of C-8 hydroxy group being sterically protected from glucuronide conjugation. The excellent potency underscores the possibility of replacing the presumed indispensable phenolic group at C-6 or C-7 of the chromene core. Co-crystal structures were obtained to highlight the change in key interactions and rationalize the retained potency.
• [EN] HYDROXYBENZOPHENONE DERIVATIVES AS HERBICIDES<br/>[FR] DERIVES D'HYDROXYBENZOPHENONES EN TANT QU'HERBICIDES
  申请人：——

  公开号：WO1998013341A1

  公开（公告）日：1998-04-02

  [EN] The invention relates to hydroxybenzophenone derivatives of formula (I), wherein R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7> and R<8> are as defined in the description, and to their use as herbicides.
  [FR] L'invention concerne des dérivés d'hydroxybenzophénones selon la formule (I). Dans cette dernière, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7> et R<8> sont tels que définis dans le descriptif. L'invention traite également de l'utilisation de ces composés comme herbicides.