N-(2-(tert-butoxycarbonylamino)phenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide | 617703-01-2

• 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-(2-(tert-butoxycarbonylamino)phenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• 英文别名: n-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide；tert-butyl N-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]amino]phenyl]carbamate
• CAS: 617703-01-2
• 化学式: C₂₄H₃₁BN₂O₅
• 分子量: 438.332
• InChiKey: CSSRUEFXNLXXIP-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(tert-butoxycarbonylamino)phenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 在 盐酸 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 9.5h， 生成 N-(2-aminophenyl)-4-[3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]-2-pyridyl]benzamide
  参考文献：
  名称：

  Flexible and Scalable Route to HDAc Inhibitors Containing an Unusual Trisubstituted Pyridine Core

  摘要：

  A scalable route to histone deacetylase inhibitors containing an unusual 2-aryl-3-cyano-5-aminomethylpyridine core has been developed which has the flexibility to deliver a range of compounds on at least a multigram scale. The key step involves a novel Mannich reaction using 3-dimethylaminoacrolein, formaldehyde, and a secondary amine to yield a 2-(alkylaminomethyl)-3-dimethylaminoacrolein. Tuning of this reaction in process development was fundamental to the success of the approach in terms of flexibility and operability on scale-up. This new methodology will also enable access an underutilised family of 3,5-disubstituted pyrid-2-ones and 2,3,5-trisubstituted pyridines.

  DOI：

  10.1021/op300021m
• 作为产物：
  描述：

  N-(2-t-butoxycarbonylaminophenyl)-4-bromobenzamide 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以100%的产率得到N-(2-(tert-butoxycarbonylamino)phenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
  参考文献：
  名称：

  [EN] BENZAMIDE DERIVATIVES USEFUL AS HISTONE DEACETYLASE INHIBITORS
  [FR] DERIVES DE BENZAMIDE UTILES EN TANT QU'INHIBITEURS D'HISTONE DEACETYLASE

  摘要：

  本发明涉及一种公式(I)的化合物，其中环A是杂环；m为0-4，每个R1是如羟基、卤素、三氟甲基和腈的基团；R2是卤素，n为0-2；每个R4是如羟基、卤素、三氟甲基和腈的基团；p为0-4；R3是氨基或羟基；或其药物可接受的盐或体内可水解的酯或酰胺及其制备过程，包含它们的药物组合物以及它们在治疗由组蛋白脱乙酰酶介导的疾病或医疗条件中的用途。

  公开号：

  WO2003087057A1

文献信息

• Novel Benzamide Derivatives
  申请人：Gibson Keith Hopkinson

  公开号：US20080119451A1

  公开（公告）日：2008-05-22

  The invention concerns benzamide derivatives of Formula (I) wherein R 1a , R 1b , R 1c , R 2 , R 3 , R 4 , integer m, integer n and W have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions which are sensitive to the inhibition of histone deacetylase (HDAC).

  这项发明涉及式（I）的苯甲酰胺衍生物，其中R1a、R1b、R1c、R2、R3、R4、整数m、整数n和W具有描述中定义的任意含义；它们的制备方法，含有它们的药物组合物以及它们在制造用作抗增殖剂的药物时的用途，用于预防或治疗对组蛋白去乙酰化酶（HDAC）抑制敏感的肿瘤或其他增殖性疾病。
• Benzamide Compounds
  申请人：Gibson Keith Hopkinson

  公开号：US20080293687A1

  公开（公告）日：2008-11-27

  The invention concerns benzamide compounds of Formula (I), wherein R 1a , R 1b , R 1c , R 2 , R 3 , R 4 , m and n have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions which are sensitive to the inhibition of histone deacetylase (HDAC).

  这项发明涉及公式（I）的苯甲酰胺化合物，其中R1a、R1b、R1c、R2、R3、R4、m和n具有描述中定义的任意含义；它们的制备过程，含有它们的药物组合物以及它们在制造用作抗增殖剂的药物时的用途，用于预防或治疗对组蛋白去乙酰化酶（HDAC）抑制敏感的肿瘤或其他增殖性疾病。
• Benzamide derivatives useful as histone deacetylase inhibitors
  申请人：Stokes Sophie Elizabeth Elaine

  公开号：US20050171103A1

  公开（公告）日：2005-08-04

  The invention concerns a compound of the formula (I) wherein Ring A is heterocyclyl; m is 0-4 and each R 1 is a group such as hydroxy, halo, trifluoromethyl and cyano; R 2 is, halo and n is 0-2; and each R 4 is a group such as hydroxy, halo, trifluoromethyl and cyano; p is 0-4; and R 3 is amino or hydroxy; or pharmaceutically-acceptable salts or in-vivo-hydrolysable ester or amide thereof processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical condions mediated by histone deacetylase.

  本发明涉及一种化合物，其化学式为（I），其中环A为杂环基；m为0-4，每个R1是羟基、卤素、三氟甲基和氰基等基团；R2为卤素，n为0-2；每个R4是羟基、卤素、三氟甲基和氰基等基团；p为0-4；R3为氨基或羟基；或其药学可接受的盐或体内可水解的酯或酰胺，以及制备它们的过程，含有它们的制药组合物以及它们在治疗组织脱乙酰化酶介导的疾病或医学状况中的用途。
• BENZAMIDE DERIVATIVES USEFUL AS HISTONE DEACETYLASE INHIBITORS
  申请人：Stokes Elaine Sophie Elizabeth

  公开号：US20090029991A1

  公开（公告）日：2009-01-29

  The invention concerns a compound of the formula (I) wherein Ring A is heterocyclyl; m is 0-4 and each R 1 is a group such as hydroxy, halo, trifluoromethyl and cyano; R 2 is halo and n is 0-2; and each R 4 is a group such as hydroxy, halo, trifluoromethyl and cyano; p is 0-4; and R 3 is amino or hydroxy; or pharmaceutically-acceptable salts or in-vivo-hydrolysable ester or amide thereof, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by histone deacetylase.

  本发明涉及式（I）的化合物，其中环A是杂环基；m为0-4，每个R1是羟基、卤素、三氟甲基和氰基等基团；R2是卤素，n为0-2；每个R4是羟基、卤素、三氟甲基和氰基等基团；p为0-4；R3是氨基或羟基；或其药学上可接受的盐或体内可水解的酯或酰胺，其制备方法，含有它们的制药组合物以及它们在通过组蛋白去乙酰化酶介导的疾病或医学情况的治疗中的应用。
• N-(2-AMINIPHENYL)-4-(5-((ETHYLAMINO)METHYL)-1,2-THIAZOL-2-YL) BENZAMIDE AND N-(2-AMINOPHENYL)-4-(5-((ISOPROPYLAMINO)METHYL)-1,2-THIAZOL-2-YL) BENZAMIDE AS HDAC INHIBITORS
  申请人：Stokes Elaine Sophie, Elizabeth

  公开号：US20090312556A1

  公开（公告）日：2009-12-17

  The invention concerns novel benzamide compounds of Formula (I): wherein R wherein is ethyl or isopropyl; or a pharmaceutically acceptable salt or pro-drug form thereof. The invention also concerns processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions, which are sensitive to the inhibition of histone deacetylase (HDAC).

  该发明涉及公式（I）的新型苯甲酰胺化合物，其中R为乙基或异丙基；或其药学上可接受的盐或前药形式。该发明还涉及制备这种化合物的方法，含有它们的制药组合物以及它们在制造用作抗增殖剂的药物中的使用，用于预防或治疗对组蛋白去乙酰化酶（HDAC）抑制敏感的肿瘤或其他增殖性疾病。