2-nitro-N-(4-(trifluoromethyl)phenyl)benzamide | 263559-07-5

• 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: 2-nitro-N-(4-(trifluoromethyl)phenyl)benzamide
• 英文别名: 2-nitro-N-(4-trifluoromethylphenyl)benzamide；2-nitro-N-[4-(trifluoromethyl)phenyl]benzamide
• CAS: 263559-07-5
• 化学式: C₁₄H₉F₃N₂O₃
• 分子量: 310.232
• InChiKey: UHWNVRNVKNHZPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-nitro-N-(4-(trifluoromethyl)phenyl)benzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 7.0h， 以97%的产率得到2-氨基-N-(4-三氟甲基苯基)苯甲酰胺
  参考文献：
  名称：

  以酰胺和脲连接基作为BCRP抑制剂的苯甲酰胺和苯基四唑衍生物的设计，合成和生物学评估

  摘要：

  乳腺癌抗性蛋白（BCRP / ABCG2）是一种72 kDa的质膜转运蛋白，是ABC转运蛋白超家族的成员。BCRP表达增加导致外排增加，因此减少了许多不相关的化学治疗剂的细胞内积累，从而导致了多药耐药性（MDR）。为了克服BCRP介导的MDR，已合成了31种具有酰胺和脲连接基的苯甲酰胺和苯基四唑衍生物，用作潜在的BCRP抑制剂。使用MTT测定法测试了目标衍生物在人非小细胞肺癌细胞系H460和米托蒽醌抗性细胞系H460 / MX20中的细胞毒性和逆转作用。在苯甲酰胺系列中，化合物6和7在10 µM的浓度下，抗折叠性分别为1.51和1.62，这与已知的BCRP抑制剂FTC相似。化合物27和31是具有酰胺接头的苯基四唑系列中最有效的类似物，在10 µM浓度下的耐折叠性分别为1.39和1.32。对于具有脲连接基的苯基四唑系列，38的抗折叠性为1.51，与FTC相似，是该系列中最有效的化合物。目标化

  DOI：

  10.1016/j.bmcl.2017.09.009
• 作为产物：
  描述：

  邻硝基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-nitro-N-(4-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  以酰胺和脲连接基作为BCRP抑制剂的苯甲酰胺和苯基四唑衍生物的设计，合成和生物学评估

  摘要：

  乳腺癌抗性蛋白（BCRP / ABCG2）是一种72 kDa的质膜转运蛋白，是ABC转运蛋白超家族的成员。BCRP表达增加导致外排增加，因此减少了许多不相关的化学治疗剂的细胞内积累，从而导致了多药耐药性（MDR）。为了克服BCRP介导的MDR，已合成了31种具有酰胺和脲连接基的苯甲酰胺和苯基四唑衍生物，用作潜在的BCRP抑制剂。使用MTT测定法测试了目标衍生物在人非小细胞肺癌细胞系H460和米托蒽醌抗性细胞系H460 / MX20中的细胞毒性和逆转作用。在苯甲酰胺系列中，化合物6和7在10 µM的浓度下，抗折叠性分别为1.51和1.62，这与已知的BCRP抑制剂FTC相似。化合物27和31是具有酰胺接头的苯基四唑系列中最有效的类似物，在10 µM浓度下的耐折叠性分别为1.39和1.32。对于具有脲连接基的苯基四唑系列，38的抗折叠性为1.51，与FTC相似，是该系列中最有效的化合物。目标化

  DOI：

  10.1016/j.bmcl.2017.09.009

文献信息

• N-aryl(thio)anthranilic acid amide derivatives, their preparation and their use as VEGF receptor tyrosine kinase inhibitors
  申请人：——

  公开号：US20020019414A1

  公开（公告）日：2002-02-14

  1 Described are compounds of formula (I), wherein W is O or S; X is NR 8 ; Y is CR 9 R 10 -(CH 2 )n wherein R 9 and R 10 are independently of each other hydrogen or lower alkyl, and n is an integer of from and including 0 to and including 3; or Y is SO 2 ; R 1 is aryl; R 2 is a mono- or bicyclic heteroaryl group comprising one or more ring nitrogen atoms with the exception that R 2 cannot represent 2-phthalimidyl, and in case of Y═SO 2 cannot represent 2,1,3-benzothiadiazol-4-yl; any of R 3 , R 4 , R 5 and R 6 , independently of the other, is H or a substituent other than hydrogen; and R 7 and R 8 , independently of each other, are H or lower alkyl; or a N-oxide or a pharmaceutically acceptable salt thereof for the preparation of a pharmaceutical product for the treatment of a neoplastic disease which responds to an inhibition of the VEGF receptor tyrosine kinase activity. The compounds of formula (I) can be used for the treatment e.g. of a neoplastic disease, such as a tumor disease, of retinopathy and age-related macular degeneration.

  描述的是化合物的结构式（I），其中W是O或S；X是NR8；Y是CR9R10-(CH2)n，其中R9和R10彼此独立地是氢或较低的烷基，n是从0到3的整数；或Y是SO2；R1是芳基；R2是一个含有一个或多个环氮原子的单环或双环杂环基团，但R2不能代表2-邻苯二甲酰胺，并且在Y为SO2的情况下不能代表2,1,3-苯并噻二唑-4-基；R3、R4、R5和R6中的任何一个，独立于其他，是H或除氢之外的取代基；R7和R8，彼此独立地是H或较低的烷基；或其N-氧化物或药用可接受的盐，用于制备用于治疗对VEGF受体酪氨酸激酶活性抑制产生反应的恶性疾病的药物产品。结构式（I）的化合物可用于治疗恶性疾病，如肿瘤疾病，视网膜病和老年性黄斑变性等。
• N-aryl (thio) anthranilic acid amide derivatives, their preparation and their use as VEGF receptor tyrosine kinase inhibitors
  申请人：——

  公开号：US20030064992A1

  公开（公告）日：2003-04-03

  1 Described are compunds of formula (I), wherein W is O or S; X is NR 8 ; Y is CR 9 R 10 —(CH 2 )n wherein R 9 and R 10 are independently of each other hydrogen or lower alkyl, and n is an integer of from and including 0 to and including 3; or Y is SO 2 ; R 1 is aryl; R 2 is a mono- or bicyclic heteroaryl group comprising one or more ring nitrogen atoms with the exception that R 2 cannot represent 2-phthalimidyl, and in case of Y=SO 2 cannot represent 2,1,3-benzothiadiazol-4-yl; any of R 3 , R 4 , R 5 and R 6 , independently of the other, is H or a substituent other than hydrogen; and R 7 and R 8 , independently of each other, are H or lower alkyl; or a N-oxide or a pharmaceutically acceptable salt thereof for the preparation of a pharmaceutical product for the treatment of a neoplastic disease which responds to an inhibition of the VEGF receptor tyrosine kinase activity. The compounds of formula (I) can be used for the treatment e.g. of a neoplastic disease, such as a tumor disease, of retinopathy and age-related macular degeneration.

  本文描述了式(I)的化合物，其中W为O或S；X为NR8；Y为CR9R10—(CH2)n，其中R9和R10独立地为氢或低碳基，n为0至3的整数，或Y为SO2；R1为芳基；R2为一个单环或双环杂芳基，其中包含一个或多个环氮原子，但R2不能代表2-苯酰亚胺基，且在Y=SO2的情况下不能代表2,1,3-苯并噻二唑-4-基；R3、R4、R5和R6中的任意一个，独立于其他的，为H或除氢以外的取代基；且R7和R8独立地为H或低碳基；或其N-氧化物或药学上可接受的盐，用于制备治疗对VEGF受体酪氨酸激酶活性抑制有反应的肿瘤疾病的药物产品。式(I)的化合物可用于治疗肿瘤疾病，如肿瘤疾病、视网膜病变和老年性黄斑变性等。
• VEGF receptor tyrosine kinase inhibitors
  申请人：Novartis AG

  公开号：US06448277B2

  公开（公告）日：2002-09-10

  Described are compounds of formula (I), wherein W is O or S; X is NR8; Y is CR9R10—(CH2)n wherein R9 and R10 are independently of each other hydrogen or lower alkyl, and n is an integer of from and including 0 to and including 3; or Y is S02; R1 is aryl; R2 is a mono- or bicyclic heteroaryl group comprising one or more ring nitrogen atoms with the exception that R2 cannot represent 2-phthalimidyl, and in case of Y=SO2 cannot represent 2,1,3-benzothiadiazol-4-yl; any of R3, R4, R5 and R6, independently of the other, is H or a substituent other than hydrogen; and R7 and R8, independently of each other, are H or lower alkyl; or a N-oxide or a pharmaceutically acceptable salt thereof for the preparation of a pharmaceutical product for the treatment of a neoplastic disease which responds to an inhibition of the VEGF receptor tyrosine kinase activity. The compounds of formula (I) can be used for the treatment e.g. of a neoplastic disease, such as a tumor disease, of retinopathy and age-related macular degeneration.

  本文描述了式（I）的化合物，其中W为O或S；X为NR8；Y为CR9R10—（CH2）n，其中R9和R10独立地为氢或低烷基，n为0至3的整数，包括0和3；或Y为S02；R1为芳基；R2为单环或双环杂芳基，包括一个或多个环氮原子，但R2不能表示2-邻苯二甲酰亚胺基，且在Y = SO2的情况下不能表示2,1,3-苯并噻二唑-4-基；R3、R4、R5和R6中的任何一个独立地为H或除氢原子以外的取代基；R7和R8独立地为H或低烷基；或其N-氧化物或药学上可接受的盐，用于制备用于治疗对VEGF受体酪氨酸激酶活性抑制有反应的肿瘤性疾病的制药产品。式（I）的化合物可用于治疗肿瘤性疾病，例如肿瘤疾病，视网膜病变和年龄相关性黄斑变性等。
• <i>N</i>²-Aroylanthranilamide Inhibitors of Human Factor Xa
  作者：Ying K. Yee、Anne Louise Tebbe、Jared H. Linebarger、Douglas W. Beight、Trelia J. Craft、Donetta Gifford-Moore、Theodore Goodson、David K. Herron、Valentine J. Klimkowski、Jeffrey A. Kyle、J. Scott Sawyer、Gerald F. Smith、Jennifer M. Tinsley、Richard D. Towner、Leonard Weir、Michael R. Wiley

  DOI：10.1021/jm990327e

  日期：2000.3.1

  Reversal of the A-ring amide link in 1,2-dibenzamidobenzene 1 (fXa K-ass = 0.81 x 10(6) L/mol) led to a series of human factor Xa (hfXa) inhibitors based on N-2-aroylanthranilamide 4. Expansion of the SAR around 4 showed that only small planar substituents could be accommodated in the A-ring for binding to the S1 site of hfXa. Bulky groups such as 4-isopropyl, 4-tert-butyl, and C-dimethylamino were favored in the B-ring to interact with the S4 site of hfXa. The central (C) ring containing a 5-methanesulfonamido group yielded greater activity than carbamoyl groups. Combining the beneficial features from the B- and C-ring SAR, compound 55 represents the most potent hfXa inhibitor in the N-2-aroylanthranilamide 4 series with hfXa K-ass = 58 x 10(6) L/mol (K-i = 11.5 nM).
• Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols
  作者：Huamin Wang、Xiangxiang Cao、Fuhong Xiao、Saiwen Liu、Guo-Jun Deng

  DOI：10.1021/ol402350x

  日期：2013.9.20

  A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reductant.