3-nitro-N-(3,4,5-trimethoxyphenyl)benzamide | 710319-44-1

• 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-nitro-N-(3,4,5-trimethoxyphenyl)benzamide
• CAS: 710319-44-1
• 化学式: C₁₆H₁₆N₂O₆
• mdl: MFCD04068325
• 分子量: 332.313
• InChiKey: LFDOKHFRMCIIAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-nitro-N-(3,4,5-trimethoxyphenyl)benzamide 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 3-amino-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  3-(2′-Bromopropionylamino)-benzamides as novel S-phase arrest agents

  摘要：

  We report the synthesis, anti proliferative activity, and SAR of novel 3-(2'-bromopropionylamino)-benzamides. Many of the benzamide compounds showed potent cytotoxicities against Molt-3 leukemia cells. Several compounds exihibited cytotoxicities (under 6.5 mu M) against five solid tumor cell lines. The mechanism of action of the most potent benzamide 101 does not involve targeting on tubulin but it causes cell cycle S-phase arrest. This active S-phase arrest agent merits further investigation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.016
• 作为产物：
  描述：

  间硝基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-nitro-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  RhIII 催化酰胺的 CH 烯丙基化和 3,4-二氢异喹啉-1(2H)-酮与 N-溴代琥珀酰亚胺的多米诺环合成

  摘要：

  用烯丙基溴在室温下开发了 RhIII 催化的缺电子芳烃、杂芳烃和烯烃的 C-H 烯丙基化反应。反应在乙醚中进行，不脱水，苯胺衍生酰胺的导向阴离子氮有助于 C-H 活化。在烯丙基化之后，通过引入的双键的分子内氨基溴化，实现了 3,4-二氢异喹啉-1(2H)-酮与 N-溴代琥珀酰亚胺 (NBS) 的多米诺循环合成。

  DOI：

  10.1002/ejoc.201501551

文献信息

• Novel diarylamides and diarylureas with N-substitution dependent activity against medulloblastoma
  作者：Christopher Lawson、Thowaiba Babikr Ahmed Alta、Georgia Moschou、Vasiliki Skamnaki、Theodora G.A. Solovou、Caroline Topham、Joseph Hayes、Timothy J. Snape

  DOI：10.1016/j.ejmech.2021.113751

  日期：2021.12
• Rh^III-Catalyzed C-H Allylation of Amides and Domino Cycling Synthesis of 3,4-Dihydroisoquinolin-1(2<i>H</i>)-ones with<i>N</i>-Bromosuccinimide
  作者：Huimin Dai、Chao Yu、Changsheng Lu、Hong Yan

  DOI：10.1002/ejoc.201501551

  日期：2016.3

  carried out in diethyl ether without dehydration, and C–H activation was assisted by the directing anionic nitrogen of the aniline-derived amide. Following the allylation, a domino cycling synthesis of 3,4-dihydroisoquinolin-1(2H)-ones with N-bromosuccinimide (NBS) through intramolecular aminobromination of the introduced double bond was achieved.

  用烯丙基溴在室温下开发了 RhIII 催化的缺电子芳烃、杂芳烃和烯烃的 C-H 烯丙基化反应。反应在乙醚中进行，不脱水，苯胺衍生酰胺的导向阴离子氮有助于 C-H 活化。在烯丙基化之后，通过引入的双键的分子内氨基溴化，实现了 3,4-二氢异喹啉-1(2H)-酮与 N-溴代琥珀酰亚胺 (NBS) 的多米诺循环合成。
• 3-(2′-Bromopropionylamino)-benzamides as novel S-phase arrest agents
  作者：Laixing Hu、Zhuo-rong Li、Jian-Nong Li、Jinrong Qu、Jian-Dong Jiang、David W. Boykin

  DOI：10.1016/j.bmcl.2007.10.016

  日期：2007.12

  We report the synthesis, anti proliferative activity, and SAR of novel 3-(2'-bromopropionylamino)-benzamides. Many of the benzamide compounds showed potent cytotoxicities against Molt-3 leukemia cells. Several compounds exihibited cytotoxicities (under 6.5 mu M) against five solid tumor cell lines. The mechanism of action of the most potent benzamide 101 does not involve targeting on tubulin but it causes cell cycle S-phase arrest. This active S-phase arrest agent merits further investigation. (c) 2007 Elsevier Ltd. All rights reserved.