N-(3,5-dimethylphenyl)-3-methoxybenzamide | 346721-60-6

• 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: N-(3,5-dimethylphenyl)-3-methoxybenzamide
• CAS: 346721-60-6
• 化学式: C₁₆H₁₇NO₂
• mdl: MFCD01152934
• 分子量: 255.316
• InChiKey: YOYXSQKGMBWPGK-UHFFFAOYSA-N

物化性质

• 沸点：
  330.8±42.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (3,5-dimethylphenyl)carbamate 在 2-氯吡啶 、 三氟甲磺酸酐 、 magnesium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 生成 N-(3,5-dimethylphenyl)-3-methoxybenzamide
  参考文献：
  名称：

  N-Alloc-、N-Boc- 和 N-Cbz 保护胺在温和条件下的实用一锅酰胺化

  摘要：

  已经描述了由N - Alloc-、N - Boc- 和N -Cbz-保护的胺轻松一锅合成酰胺。该反应涉及使用在 2-氯吡啶和三氟甲磺酰酐存在下原位生成的异氰酸酯中间体与格氏试剂反应生成相应的酰胺。使用该反应方案，多种N - Alloc-、N - Boc- 和N -Cbz-保护的脂肪胺和芳基胺以高产率有效地转化为酰胺。该方法对酰胺的合成非常有效，并为简便的酰胺化提供了一种有前途的方法。

  DOI：

  10.1039/d1ra02242c

文献信息

• NOVEL BIARYLAMIDE DERIVATIVE AND COMPOSITIONS CONTAINING THE DERIVATIVE AS AN ACTIVE INGREDIENT
  申请人：Shin Dong Heon

  公开号：US20120289595A1

  公开（公告）日：2012-11-15

  The present invention relates to a novel biarylamide derivative and a pharmaceutical composition or a cosmetic composition comprising the same as an active ingredient. More particularly, the present invention relates to a novel biarylamide derivative, a pharmaceutical composition or a cosmetic composition for preventing or treating a pigmentation disorder caused by an abnormal excess of melanin or a disease caused by melanocyte hyperplasia comprising the same as an active ingredient. The biarylamide derivative of the present invention inhibits melanin production and thus inhibits melanocyte hyperplasia. Therefore, a cosmetic composition comprising the biarylamide is excellent in a whitening effect, and a pharmaceutical composition comprising the biarylamide is effective in the prevention or treatment of pigmentation disorders of skin such as lentigo, melasma, freckle, etc. and malignant melanoma.

  本发明涉及一种新型二芳基酰胺衍生物，以及包含其作为活性成分的制药组合物或化妆品组合物。更具体地，本发明涉及一种新型二芳基酰胺衍生物，以及包含其作为活性成分的制药组合物或化妆品组合物，用于预防或治疗由于黑色素异常过多引起的色素沉着障碍或由黑色素细胞增生引起的疾病。本发明的二芳基酰胺衍生物抑制黑色素的生成，从而抑制黑色素细胞增生。因此，包含该二芳基酰胺的化妆品组合物具有出色的美白效果，包含该二芳基酰胺的制药组合物对皮肤色素沉着障碍如雀斑、黄褐斑等和恶性黑色素瘤的预防或治疗具有良好的效果。
• Identification of a potent and noncytotoxic inhibitor of melanin production
  作者：Soonho Hwang、Sang Yoon Choi、Jin Hee Lee、Shinae Kim、Jinkyung In、Sang Keun Ha、Eunjung Lee、Tae-Yoon Kim、Sun Yeou Kim、Sun Choi、Sanghee Kim

  DOI：10.1016/j.bmc.2010.06.034

  日期：2010.8

  On the basis of a hit from random screening, biaryl amide derivatives were prepared in a combinatorial manner via parallel solution-phase synthesis, and their effects on melanocytes were investigated to discover new effective skin depigmenting agents. Among the 120 derivatives prepared, five members exhibited a >30% reduction of melanin production at 30 mu M with a cell viability of >90%. In particular, compound A(3)/B-5 exhibited effective inhibitory activity on melanin synthesis. Although the inhibition percentage of A(3)/B-5 was slightly lower than that of the positive reference compound, phenylthiourea (PTU), A(3)/B-5 demonstrated a much better cell viability than PTU. In vivo evaluation of A(3)/B-5 also showed a significant decrease of melanin pigments. In addition, the in silico classification model was built based on the experimental data of library members. Our results suggest that these biaryl amide derivatives may act as potent skin depigmenting agents. (C) 2010 Elsevier Ltd. All rights reserved.
• US8552065B2
  申请人：——

  公开号：US8552065B2

  公开（公告）日：2013-10-08
• [EN] WHITENING ABILITY OF SMALL STEM CELL AND USE THEREOF<br/>[FR] CAPACITÉ DE BLANCHIMENT DE PETITES CELLULES SOUCHES ET LEUR UTILISATION<br/>[KO] 작은 크기의 줄기세포의 미백능 및 이의 용도
  申请人：MEDIPOST CO LTD

  公开号：WO2015190808A2

  公开（公告）日：2015-12-17

  본 발명은 크기가 작은 줄기세포, 특히, 직경 8㎛이하의 작은 줄기세포 또는 이의 배양액을 유효성분으로 함유하는 미백용 조성물, 이의 제조 방법 및 이의 용도에 관한 것으로, 상기 직경 8㎛이하의 크기가 작은 줄기세포가 보유하고 있는, 유난히 현저하게 멜라닌 양을 감소시키는 미백 기능을 이용하는 용도에 관한 것이다.
• Practical one-pot amidation of <i>N</i>-Alloc-, <i>N</i>-Boc-, and <i>N</i>-Cbz protected amines under mild conditions
  作者：Wan Pyo Hong、Van Hieu Tran、Hee-Kwon Kim

  DOI：10.1039/d1ra02242c

  日期：——

  A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and

  已经描述了由N - Alloc-、N - Boc- 和N -Cbz-保护的胺轻松一锅合成酰胺。该反应涉及使用在 2-氯吡啶和三氟甲磺酰酐存在下原位生成的异氰酸酯中间体与格氏试剂反应生成相应的酰胺。使用该反应方案，多种N - Alloc-、N - Boc- 和N -Cbz-保护的脂肪胺和芳基胺以高产率有效地转化为酰胺。该方法对酰胺的合成非常有效，并为简便的酰胺化提供了一种有前途的方法。