1-cyclopropyl-3-(3-nitrophenyl)urea | 64393-00-6

• 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: 1-cyclopropyl-3-(3-nitrophenyl)urea
• 英文别名: N-(3-nitrophenyl)-N'-cyclopropyl urea；1-Cyclopropyl-3-(3-nitrophenyl)-harnstoff；1-cyclopropyl-3-(nitrophenyl)urea；3-Cyclopropyl-1-(3-nitrophenyl)urea
• CAS: 64393-00-6
• 化学式: C₁₀H₁₁N₃O₃
• mdl: MFCD06106005
• 分子量: 221.216
• InChiKey: UHEYQOOFVUXABF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-3-(3-nitrophenyl)urea 在 tin(II) chloride dihdyrate 、 硫酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.5h， 生成 2-amino-1-(3-(3-cyclopropylureido)phenyl)-1H-pyrrolo[2,3-b]quinoxaline-3-carboxamide
  参考文献：
  名称：

  Pyrrolo[3,2-b]quinoxaline Derivatives as Types I_1/2 and II Eph Tyrosine Kinase Inhibitors: Structure-Based Design, Synthesis, and in Vivo Validation

  摘要：

  The X-ray crystal structures of the catalytic domain of the EphA3 tyrosine kinase in complex with two type I inhibitors previously discovered in silico (compounds A and B) were used to design type I-1/2 and II inhibitors. Chemical synthesis of about 25 derivatives culminated in the discovery of compounds 11d (type I-1/2), 7b, and 7g (both of type II), which have low-nanomolar affinity for Eph kinases in vitro and a good selectivity profile on a panel of 453 human kinases (395 nonmutant). Surface plasmon resonance measurements show a very slow unbinding rate (1/115 min) for inhibitor 7m. Slow dissociation is consistent with a type II binding mode in which the hydrophobic moiety (trifluoromethyl-benzene) of the inhibitor is deeply buried in a cavity originating from the displacement of the Phe side chain of the so-called DFG motif as observed in the crystal structure of compound 7m. The inhibitor 11d displayed good in vivo efficacy in a human breast cancer xenograft.

  DOI：

  10.1021/jm5009242
• 作为产物：
  描述：

  3-硝基苯异氢酸酯 以99的产率得到1-cyclopropyl-3-(3-nitrophenyl)urea
  参考文献：
  名称：

  Pyrimidine compound and medical use thereof

  摘要：

  本发明涉及一种嘧啶化合物或其药学上可接受的盐，其由以下式[I]表示，其中每个符号如规范中所定义，并且涉及一种治疗或预防不良细胞增殖的方法，包括给予此类化合物。本发明的化合物在抑制不良细胞增殖，特别是抗肿瘤活性方面具有优越的活性，并且可用作抗肿瘤剂，用于预防或治疗癌症、风湿病等。此外，本发明的化合物在与其他抗肿瘤剂如烷基化剂或代谢拮抗剂联合使用时，可成为更有效的抗肿瘤剂。

  公开号：

  US08835443B2

文献信息

• [EN] 5-AMINO-2,4,7-TRIOXO-3,4,7,8-TETRAHYDRO-2H-PYRIDO'2,3-D! PYRIMIDINE DERIVATIVES AND RELATED COMPOUNDS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE 5-AMINO-2,4,7-TRIOXO-3,4,7,8-TÉTRAHYDRO-2H-PYRIDO'2,3-D! PYRIMIDINE ET COMPOSÉS APPARENTÉS POUR LE TRAITEMENT DU CANCER
  申请人：JAPAN TOBACCO INC

  公开号：WO2005121142A1

  公开（公告）日：2005-12-22

  The present invention relates to a pyrimidine compound represented by the following formula [I] wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, and a pharmaceutical agent for the prophylaxis or treatment of a disease caused by undesirable cell proliferation, particularly an antitumor agent, which contains such compound. The compound of the present invention has superior undesirable cell proliferation suppressing action, particularly, an antitumor action, and is useful as an antitumor agent for the prophylaxis or treatment of cancer, antirheumatoid agent and the like. In addition, by the combined use with other antitumor agent such as alkylating agent, metabolism antagonist and the like, it can be a more effective antitumor agent.

  本发明涉及一种由以下式[I]表示的嘧啶化合物，其中每个符号如规范中所定义，其药学上可接受的盐，以及用于预防或治疗由不良细胞增殖引起的疾病的药物剂，特别是一种抗肿瘤剂，其中包含这种化合物。本发明的化合物具有优越的不良细胞增殖抑制作用，特别是抗肿瘤作用，并且可用作预防或治疗癌症的抗肿瘤剂，抗风湿剂等。此外，通过与其他抗肿瘤剂如烷化剂、代谢拮抗剂等的联合使用，可以使其成为更有效的抗肿瘤剂。
• 一种合成曲美替尼的方法
  申请人：安庆奇创药业有限公司

  公开号：CN109320513B

  公开（公告）日：2021-03-16

  本发明公开了一种曲美替尼的合成方法，采用N‑(2‑氟‑4‑碘苯基)‑N’‑甲基脲脱水成碳二亚胺后，与2‑甲基‑3‑氧代‑戊二酸二乙酯进行环合反应得2‑(2‑氟‑4‑碘苯基氨基)‑4‑羟基‑1,5‑二甲基‑6‑氧代‑1,6‑二氢吡啶‑3‑羧酸乙酯；然后与N‑(3‑硝基苯基)‑N’‑环丙基脲进行环合得3‑环丙基‑5‑(2‑氟‑4‑碘苯基氨基)‑6,8‑甲基‑1‑(3‑硝基苯基)吡啶并[4,3‑d]嘧啶‑2,4,7(1H,3H,6H)‑三酮；最后先还原硝基，再进行乙酰化即得曲美替尼。本发明通过逆合成分析，提出了一种曲美替尼的合成新路线，可以大大缩短工艺流程，且制备过程中未使用昂贵试剂，具有操作简便，成本较低的优势，为曲美替尼的制备提供了参考。
• PYRIMIDINE COMPOUND AND MEDICAL USE THEREOF
  申请人：Kawasaki Hisashi

  公开号：US20080312228A1

  公开（公告）日：2008-12-18

  The present invention relates to a pyrimidine compound or a pharmaceutically acceptable salt thereof represented by the following formula [I] wherein each symbol is as defined in the specification and a method of therapeutically or prophylactically treating an undesirable cell proliferation, comprising administering such a compound. The compound of the present invention has superior activity in suppressing undesirable cell proliferation, particularly, an antitumor activity, and is useful as an antitumor agent for the prophylaxis or treatment of cancer, rheumatism, and the like. In addition, the compound of the present invention can be a more effective antitumor agent when used in combination with other antitumor agents such as an alkylating agent or metabolism antagonist.

  本发明涉及一种嘧啶化合物或其药学上可接受的盐，其由以下公式[I]所表示，其中每个符号如规范中所定义，并提供了一种治疗或预防不良细胞增殖的方法，包括给予这种化合物。本发明的化合物在抑制不良细胞增殖，特别是抗肿瘤活性方面具有优越性，并且可用作抗肿瘤剂，用于预防或治疗癌症、风湿病等。此外，本发明的化合物在与其他抗肿瘤剂如烷基化剂或代谢拮抗剂联合使用时，可成为更有效的抗肿瘤剂。
• PYRIMIDINE COMPOUND AND MEDICAL USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：US20150183812A1

  公开（公告）日：2015-07-02

  The present invention relates to a pyrimidine compound or a pharmaceutically acceptable salt thereof represented by the following formula [I] wherein each symbol is as defined in the specification and a method of therapeutically or prophylactically treating an undesirable cell proliferation, comprising administering such a compound. The compound of the present invention has superior activity in suppressing undesirable cell proliferation, particularly, an antitumor activity, and is useful as an antitumor agent for the prophylaxis or treatment of cancer, rheumatism, and the like. In addition, the compound of the present invention can be a more effective antitumor agent when used in combination with other antitumor agents such as an alkylating agent or metabolism antagonist.

  本发明涉及一种由以下式[I]所表示的嘧啶化合物或其药学上可接受的盐，其中每个符号如规范中所定义，以及治疗或预防不良细胞增殖的方法，包括给予这样的化合物。本发明的化合物在抑制不良细胞增殖，特别是抗肿瘤活性方面具有优越性，并且在预防或治疗癌症、风湿病等方面作为抗肿瘤剂非常有用。此外，本发明的化合物在与其他抗肿瘤剂如烷基化剂或代谢拮抗剂联合使用时，可以更有效地作为抗肿瘤剂。
• 5-amino-2,4,7-trioxo-3,4,7,8-tetrahydro-2H-pyrido[2,3-d]pyrimidine derivatives and related compounds for the treatment of cancer
  申请人：Japan Tobacco, Inc.

  公开号：EP2298768A1

  公开（公告）日：2011-03-23

  The present invention relates to a pyrimidine compound represented by the following formula [I] wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, and a pharmaceutical agent for the prophylaxis or treatment of a disease caused by undesirable cell proliferation, particularly an antitumor agent, which contains such compound. The compound of the present invention has superior undesirable cell proliferation suppressing action, particularly, an antitumor action, and is useful as an antitumor agent for the prophylaxis or treatment of cancer, antirheumatoid agent and the like. In addition, by the combined use with other antitumor agent such as alkylating agent, metabolism antagonist and the like, it can be a more effective antitumor agent.

  本发明涉及一种由下式[I]表示的嘧啶化合物 其中各符号如说明书中所定义，其药学上可接受的盐，以及含有这种化合物的用于预防或治疗由不良细胞增殖引起的疾病的药剂，特别是抗肿瘤药剂。本发明的化合物具有优异的抑制不良细胞增殖的作用，特别是抗肿瘤作用，可用作预防或治疗癌症的抗肿瘤剂、抗类风湿剂等。此外，通过与其他抗肿瘤剂（如烷化剂、代谢拮抗剂等）联合使用，它可以成为一种更有效的抗肿瘤剂。