4-methyl-N-(3,4,5-trimethoxyphenyl)benzamide

• 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: 4-methyl-N-(3,4,5-trimethoxyphenyl)benzamide
• 化学式: C₁₇H₁₉NO₄
• mdl: MFCD04068331
• 分子量: 301.342
• InChiKey: YFEAXSRDPIBZOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(3,4,5-trimethoxyphenyl)benzamide 在 叔丁基过氧化氢 、 copper(l) iodide 、 叠氮基三甲基硅烷 作用下， 以 癸烷 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以86%的产率得到4-methyl-N-(3,4,5-trimethoxy-2-nitrophenyl)benzamide
  参考文献：
  名称：

  在有氧条件下，通过TMS叠氮化物和TBHP的同时氧化-氧化，在芳基CH键上进行铜催化的直接硝化

  摘要：

  通过直接的C Ar -H功能化，开发出了前所未有的铜催化原位叠氮化氧化技术，用于苯胺和磺酰胺的硝化。使用TMSN 3和TBHP可以实现这种新颖而高效的硝化方案，而不会排除空气或湿气。已经研究了2-硝基苯胺的合成应用。

  DOI：

  10.1021/acs.orglett.7b01489
• 作为产物：
  描述：

  对甲基苯甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 4-methyl-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest

  摘要：

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.

  DOI：

  10.1021/ja042913p

文献信息

• Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
  作者：Anudeep Kumar Narula、Ashmita Singh

  DOI：10.1055/a-1343-5203

  日期：2021.4

  one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible

  已经开发了一种一锅两步氧化方法，用于叔丁基氢过氧化物介导的碘化铜（I）和N-杂环卡宾催化的醛和胺向酰胺的转化。该方法是无添加剂的，不需要将胺转化为其盐酸盐。该方法简单实用，底物范围广，使用经济，可行，试剂丰富。
• Stable and Reusable Binaphthyl‐Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides
  作者：Nidhi Sharma、Govindasamy Sekar

  DOI：10.1002/adsc.201500642

  日期：2016.1.21

  A binaphthyl‐supported Pd nanoparticles (Pd‐BNP)‐catalyzed aminocarbonylation of aryl iodides in the presence of carbon monoxide and amines for the synthesis of amides has been developed. This methodology provides an efficient route for the synthesis of a COX‐2 enzyme inhibitor having anti‐inflammatory activity.

  已经开发了在二氧化碳和胺存在下，联萘负载的Pd纳米颗粒（Pd-BNP）催化的芳基碘的氨基羰基化反应，用于合成酰胺。这种方法为合成具有抗炎活性的COX-2酶抑制剂提供了一条有效途径。
• [EN] COMPOUNDS AND METHODS FOR TREATMENT OF CANCER AND MODULATION OF PROGRAMMED CELL DEATH FOR MELANOMA AND OTHER CANCER CELLS<br/>[FR] COMPOSES ET PROCEDES DE TRAITEMENT DU CANCER ET MODULATION DE LA MORT CELLULAIRE PROGRAMMEE DE MELANOMES ET D'AUTRES CELLULES CANCEREUSES
  申请人：UNIV ALABAMA

  公开号：WO2005044191A3

  公开（公告）日：2005-10-20
• Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest
  作者：Robin S. Dothager、Karson S. Putt、Brittany J. Allen、Benjamin J. Leslie、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja042913p

  日期：2005.6.1

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.
• Copper-Catalyzed Direct Nitration on Aryl C–H Bonds by Concomitant Azidation–Oxidation with TMS Azide and TBHP under Aerobic Conditions
  作者：Botla Vinayak、Malapaka Chandrasekharam

  DOI：10.1021/acs.orglett.7b01489

  日期：2017.7.7

  An unprecedented copper-catalyzed in situ azidation–oxidation for the nitration of anilides and sulfonamides has been developed by direct CAr–H functionalization. This novel and efficient nitration protocol is achieved employing TMSN3 and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.

  通过直接的C Ar -H功能化，开发出了前所未有的铜催化原位叠氮化氧化技术，用于苯胺和磺酰胺的硝化。使用TMSN 3和TBHP可以实现这种新颖而高效的硝化方案，而不会排除空气或湿气。已经研究了2-硝基苯胺的合成应用。