4-(aminocarbonyl)-3-(cyclobutylamino)benzoic acid | 1149384-15-5

• 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: 4-(aminocarbonyl)-3-(cyclobutylamino)benzoic acid
• 英文别名: 4-carbamoyl-3-(cyclobutylamino)benzoic acid
• CAS: 1149384-15-5
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: OZVQZYPQTXTDOK-UHFFFAOYSA-N

物化性质

• 沸点：
  467.0±40.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(aminocarbonyl)-3-(cyclobutylamino)benzoic acid 、 6-(3-amino-8-azabicyclo[3.2.1]octan-8-yl)-N-[(1S)-1-[4-(4-methylpiperazin-1-yl)phenyl]ethyl]pyridine-3-carboxamide 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(cyclobutylamino)-4-N-[8-[5-[[(1S)-1-[4-(4-methylpiperazin-1-yl)phenyl]ethyl]carbamoyl]pyridin-2-yl]-8-azabicyclo[3.2.1]octan-3-yl]benzene-1,4-dicarboxamide
  参考文献：
  名称：

  Discovery of XL888: A novel tropane-derived small molecule inhibitor of HSP90

  摘要：

  With structural guidance, tropane-derived HTS hits were modified to optimize for HSP90 inhibition and a desirable in vivo profile. Through an iterative SAR development process 12i (XL888) was discovered and shown to reduce HSP90 client protein content in PD studies. Furthermore, efficacy experiments performed in a NCI-N87 mouse xenograft model demonstrated tumor regression in some dosing regimens. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.052
• 作为产物：
  描述：

  3-溴-4-氰基苯甲酸乙酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 双氧水 、 potassium carbonate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 生成 4-(aminocarbonyl)-3-(cyclobutylamino)benzoic acid
  参考文献：
  名称：

  Discovery of XL888: A novel tropane-derived small molecule inhibitor of HSP90

  摘要：

  With structural guidance, tropane-derived HTS hits were modified to optimize for HSP90 inhibition and a desirable in vivo profile. Through an iterative SAR development process 12i (XL888) was discovered and shown to reduce HSP90 client protein content in PD studies. Furthermore, efficacy experiments performed in a NCI-N87 mouse xenograft model demonstrated tumor regression in some dosing regimens. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.052

文献信息

• [EN] TROPANE COMPOUNDS<br/>[FR] COMPOSÉS DE TROPANE
  申请人：EXELIXIS INC

  公开号：WO2009055077A1

  公开（公告）日：2009-04-30

  A compound according to Formula I or II: (I) or (II) wherein R1, R1b, R2, L1, and L2 and L2b are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

  根据公式I或II的化合物：（I）或（II），其中R1、R1b、R2、L1和L2以及L2b的定义如规范中所述，以及其药物组合物和使用方法。
• Tropane compounds
  申请人：Rice Kenneth D.

  公开号：US20090163471A1

  公开（公告）日：2009-06-25

  A compound according to Formula I or II: wherein R 1 , R 1b , R 2 , L 1 , and L 2 and L 2b are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

  一种符合公式I或II的化合物：其中R1，R1b，R2，L1和L2以及L2b的定义如规范所述，以及其制药组成物和使用方法。
• TROPANE COMPOUNDS
  申请人：Exelixis, Inc.

  公开号：EP2074120A1

  公开（公告）日：2009-07-01
• US8012956B2
  申请人：——

  公开号：US8012956B2

  公开（公告）日：2011-09-06
• Discovery of XL888: A novel tropane-derived small molecule inhibitor of HSP90
  作者：Joerg Bussenius、Charles M. Blazey、Naing Aay、Neel K. Anand、Arlyn Arcalas、TaeGon Baik、Owen J. Bowles、Chris A. Buhr、Simona Costanzo、Jeffrey K. Curtis、Steven C. DeFina、Larisa Dubenko、Timothy S. Heuer、Ping Huang、Christopher Jaeger、Anagha Joshi、Abigail R. Kennedy、Angie I. Kim、Katherine Lara、Jae Lee、Jonathan Li、Julie C. Lougheed、Sunghoon Ma、Shiva Malek、Jean-Claire L. Manalo、Jean-Francois Martini、Garth McGrath、Monique Nicoll、John M. Nuss、Michael Pack、Csaba J. Peto、Tsze H. Tsang、Longcheng Wang、Scott W. Womble、Michael Yakes、Wentao Zhang、Kenneth D. Rice

  DOI：10.1016/j.bmcl.2012.07.052

  日期：2012.9

  With structural guidance, tropane-derived HTS hits were modified to optimize for HSP90 inhibition and a desirable in vivo profile. Through an iterative SAR development process 12i (XL888) was discovered and shown to reduce HSP90 client protein content in PD studies. Furthermore, efficacy experiments performed in a NCI-N87 mouse xenograft model demonstrated tumor regression in some dosing regimens. (C) 2012 Elsevier Ltd. All rights reserved.