3-methyl-4-cyano-N,N-dimethylaniline | 57413-39-5

• 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-methyl-4-cyano-N,N-dimethylaniline
• 英文别名: m-Methyl-p-Cyanodemethylanilin；4-Cyan-3,N,N-trimethyl-anilin；4-(dimethylamino)-2-methylbenzonitrile
• CAS: 57413-39-5
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD18917312
• 分子量: 160.219
• InChiKey: AXADDPXGCNTXLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-4-cyano-N,N-dimethylaniline 在 tetraphosphorus decasulfide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 4-(dimethylamino)-2-methylbenzenecarbothioamide
  参考文献：
  名称：

  2-Aryl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols as a class of antitumor agents selectively active in securin−/− cells

  摘要：

  A series of 2-(4-aminophenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols have been developed as antitumor agents that showed high selectivity against aneuploid cell lines (vs diploid cell lines). Structure-activity relationship studies showed that a hydroxymethyl group at the 2- position of the phenyl ring increased potency and selectivity. A pyrrolidinyl group at the 4-position of the phenyl ring was comparable to a dimethylamino group. The corresponding 5-aza analogs, 2-(4-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridin-7-ols, retained potency and high level of selectivity against aneuploid cell growth (vs diploid cells). These 5-aza compounds exhibited higher water solubility and higher metabolic stability than the corresponding carba analogs. Compound 19 showed the highest potency against MCF-7 and MDA-MB-361 lines and was selected for further evaluation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.021
• 作为产物：
  描述：

  3-碘-2-甲基苯甲腈 、 O-benzoyl-N,N-dimethylhydroxylamine 在 norbornene 、 三(4-甲氧苯基)膦 、 palladium diacetate 、 caesium carbonate 、 环己醇 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到3-methyl-4-cyano-N,N-dimethylaniline
  参考文献：
  名称：

  模板合成解决芳基碘不可达邻位C-H官能化反应

  摘要：

  该报告描述了使用简单的 Pd/NBE 催化系统通过模板转化反应实现芳基碘的邻位C-H 氧基化和膦酰化以及其他功能化。通过C-H胺化在芳基碘化物的邻位引入二甲胺，芳基二甲胺迅速转化为甲基季铵盐沉淀。甲基季铵盐避免了后续官能化中的霍夫曼消除。该方法间接解决了Pd/NBE化学领域长期以来未能实现的各种芳基碘化物邻位官能化反应。

  DOI：

  10.1021/acs.joc.3c02014

文献信息

• [EN] 2-ARYL- AND 2-HETEROARYLTHIAZOLYL COMPOUNDS, METHODS FOR THEIR PREPARATION AND USE THEREOF<br/>[FR] COMPOSÉS DE 2-ARYL- ET DE 2-HÉTÉROARYL-THIAZOLYLE, LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：WYETH CORP

  公开号：WO2009120826A1

  公开（公告）日：2009-10-01

  The present invention discloses fused bicyclic 2-aryl- or 2-heteroarylthiazolyl compounds and their pharmaceutically acceptable salts and esters thereof, which are useful for inhibiting the growth of cancerous cells, inhibiting human breast carcinoma tumor growth in particular and to treat diseases or disorders associated with securin, including elevated securin levels.

  本发明揭示了融合的双环2-芳基或2-杂环芳基噻唑基化合物及其药用盐和酯，这些化合物对抑制癌细胞的生长、特别是抑制人类乳腺癌肿瘤的生长以及治疗与分泌蛋白相关的疾病或紊乱，包括高水平的分泌蛋白水平具有用处。
• 2-Aryl- and 2-Heteroarylthiazolyl Compounds, Methods for Their Preparation and Use Thereof
  申请人：Zhang Nan

  公开号：US20090270363A1

  公开（公告）日：2009-10-29

  The present invention discloses fused bicyclic 2-aryl- or 2-heteroarylthiazolyl compounds and their pharmaceutically acceptable salts and esters thereof, which are useful for inhibiting the growth of cancerous cells, inhibiting human breast carcinoma tumor growth in particular and to treat diseases or disorders associated with securin, including elevated securin levels.

  本发明公开了融合的双环2-芳基-或2-杂环基硫唑基化合物及其药学上可接受的盐和酯，其对抑制癌细胞生长、特别是对抑制人类乳腺癌肿瘤生长以及治疗与分离素有关的疾病或疾病相关障碍，包括升高的分离素水平具有用处。
• NEW SUBSTITUTED BIPHENYL ANALOGUES AS DUAL INHIBITORS OF AROMATASE AND SULFATASE
  申请人：BEAUFOUR IPSEN TIANJIN PHARMACEUTICAL CO., LTD

  公开号：US20170001964A1

  公开（公告）日：2017-01-05

  The present invention relates to new biphenyl derivatives of formula These compounds acting as aromatase and sulfatase inhibitors, they are particularly useful for treating pathological conditions or diseases in which aromatase and sulfatase are involved. Moreover, the present invention provides processes for the preparation of these compounds. The invention also relates to pharmaceutical compositions containing said products and their use for the preparation of a medicament, in particular for the treatment of diseases characterized by aromatase and sulfatase activity such as hormone-dependent cancers.
• US9682941B2
  申请人：——

  公开号：US9682941B2

  公开（公告）日：2017-06-20
• 2-Aryl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols as a class of antitumor agents selectively active in securin−/− cells
  作者：Nan Zhang、Semiramis Ayral-Kaloustian、Chuansheng Niu、Thai Nguyen、Erik Upeslacis、Tarek S. Mansour、Shoba Ragunathan、Edward Rosfjord

  DOI：10.1016/j.bmcl.2010.05.021

  日期：2010.7

  A series of 2-(4-aminophenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols have been developed as antitumor agents that showed high selectivity against aneuploid cell lines (vs diploid cell lines). Structure-activity relationship studies showed that a hydroxymethyl group at the 2- position of the phenyl ring increased potency and selectivity. A pyrrolidinyl group at the 4-position of the phenyl ring was comparable to a dimethylamino group. The corresponding 5-aza analogs, 2-(4-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridin-7-ols, retained potency and high level of selectivity against aneuploid cell growth (vs diploid cells). These 5-aza compounds exhibited higher water solubility and higher metabolic stability than the corresponding carba analogs. Compound 19 showed the highest potency against MCF-7 and MDA-MB-361 lines and was selected for further evaluation. (c) 2010 Elsevier Ltd. All rights reserved.