6-氯-1-苯并呋喃-7-胺 | 379230-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 6-氯-1-苯并呋喃-7-胺
• 英文名称: 6-chloro-1-benzofuran-7-amine
• 英文别名: 6-chlorobenzofuran-7-amine；7-amino-6-chlorobenzofuran
• CAS: 379230-43-0
• 化学式: C₈H₆ClNO
• mdl: MFCD09038113
• 分子量: 167.595
• InChiKey: HLBZNYOCYAXWMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氯-1-苯并呋喃-7-胺 、 4-氯-6-甲氧基-7-[3-(4-吗啉)丙氧基]喹唑啉 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以67%的产率得到4-(6-chlorobenzofuran-7-ylamino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline
  参考文献：
  名称：

  Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src

  摘要：

  Deregulated activity of the nonreceptor tyrosine kinase c-Src is believed to result in signal transduction, cytoskeletal and adhesion changes, ultimately promoting a tumor-invasive phenotype. We report here the discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of the c-Src enzyme. Special attention was directed toward finding inhibitors selective against KDR tyrosine kinase in order to ensure that the in vivo profile of a specific Src inhibitor could be determined. The 4-aminobenzodioxole quinazoline series gave compounds with excellent potency and selectivity. The most interesting compounds were evaluated in vivo and displayed good pharmacokinetics following oral dosing. Compounds such as the aminobenzodioxoles were shown to be potent inhibitors of tumor growth in a c-Src-transformed 3T3 xenograft model in vivo, resulting in more than 90% growth inhibition at doses as low as 6 mg/kg po once daily. Src tyrosine kinase inhibitors such as these may provide a novel therapeutic modality for targeting cancer invasion and metastasis.

  DOI：

  10.1021/jm030317k
• 作为产物：
  描述：

  2-氨基-6-氯苯甲酸乙酯 在 氢氧化钾 、 磷酸 、 硫酸 、 二苯基磷酸 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 臭氧 、 三乙胺 、 叔丁醇 、 sodium nitrite 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 43.16h， 生成 6-氯-1-苯并呋喃-7-胺
  参考文献：
  名称：

  Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src

  摘要：

  Deregulated activity of the nonreceptor tyrosine kinase c-Src is believed to result in signal transduction, cytoskeletal and adhesion changes, ultimately promoting a tumor-invasive phenotype. We report here the discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of the c-Src enzyme. Special attention was directed toward finding inhibitors selective against KDR tyrosine kinase in order to ensure that the in vivo profile of a specific Src inhibitor could be determined. The 4-aminobenzodioxole quinazoline series gave compounds with excellent potency and selectivity. The most interesting compounds were evaluated in vivo and displayed good pharmacokinetics following oral dosing. Compounds such as the aminobenzodioxoles were shown to be potent inhibitors of tumor growth in a c-Src-transformed 3T3 xenograft model in vivo, resulting in more than 90% growth inhibition at doses as low as 6 mg/kg po once daily. Src tyrosine kinase inhibitors such as these may provide a novel therapeutic modality for targeting cancer invasion and metastasis.

  DOI：

  10.1021/jm030317k

文献信息

• Quinazoline derivatives with anti-tumour activity
  申请人：AstraZeneca AB

  公开号：US20040048881A1

  公开（公告）日：2004-03-11

  The invention concerns quinazoline derivatives of Formula I 1 wherein each of m, R 1 , n, R 2 and R 3 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 anti-invasive agent in the containment and/or treatment of solid tumour disease.

  这项发明涉及式I的喹唑啉衍生物，其中m、R1、n、R2和R3中的每一个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侵袭剂的药物的过程中在固体肿瘤疾病的控制和/或治疗中的使用。
• PYRIMIDINE DERIVATIVES
  申请人：Kettle Jason Grant

  公开号：US20110046108A1

  公开（公告）日：2011-02-24

  The invention concerns benzamide compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R 1 , ring A, n, R 3 , and R 4 are as defined in the description. The present invention also relates to 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 EphB4, and/or EphA2 and/or Src kinases.

  这项发明涉及Formula (I)的苯甲酰胺化合物或其药用可接受的盐，其中R1、环A、n、R3和R4如描述中所定义。本发明还涉及制备这种化合物的方法、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中的用途，用于预防或治疗对EphB4、EphA2和/或Src激酶抑制敏感的肿瘤或其他增殖病症。
• [EN] QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF T CELL MEDIATED DISEASES<br/>[FR] DERIVES DE QUINAZOLINE DESTINES AU TRAITEMENT DES MALADIES INDUITES PAR LES LYMPHOCYTES T
  申请人：ASTRAZENECA AB

  公开号：WO2003045395A1

  公开（公告）日：2003-06-05

  The invention concerns the use of the quinazoline derivatives of Formula (I) wherein each of Q1, Z, m, R1, R2, R3 and Q2 have any of the meanings defined in the description in the manufacture of a medicament for use in the prevention or treatment of T cell mediated diseases or medical conditions in a warm-blooded animal.

  本发明涉及使用式（I）中各自具有定义于本说明书中的任何含义的Q1、Z、m、R1、R2、R3和Q2的喹唑啉衍生物制造用于预防或治疗温血动物的T细胞介导疾病或医疗情况的药物。
• [EN] QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF TUMOURS<br/>[FR] DERIVES DE LA QUINAZOLINE POUR LE TRAITEMENT DE TUMEURS
  申请人：ASTRAZENECA AB

  公开号：WO2001094341A1

  公开（公告）日：2001-12-13

  The invention concerns quinazoline derivatives of Formula (I) wherein each of Q1, Z, m, R?1, R2, R3 and Q2¿ 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 anti-invasive agent in the containment and/or treatment of solid tumour disease.

  本发明涉及公式（I）的喹唑啉衍生物，其中Q1，Z，m，R?1，R2，R3和Q2¿中的每一个都具有描述中定义的任何含义；制备它们的过程，含有它们的制药组合物以及它们在制造用于抗侵袭剂的药物，用于包含和/或治疗实体肿瘤疾病。
• Quinazoline derivatives for treatment of tumours
  申请人：——

  公开号：US20040214841A1

  公开（公告）日：2004-10-28

  The invention concerns quinazoline derivatives of Formula (I) wherein each of Q 1 , Z, m, R 1 , R 2 , R 3 and Q 2 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 anti-invasive agent in the containment and/or treatment of solid tumour disease. 1

  本发明涉及公式（I）的喹嗪衍生物，其中Q1、Z、m、R1、R2、R3和Q2中的每个都具有描述中定义的任何含义；制备它们的过程，包含它们的制药组合物以及它们在制造用于抗侵袭剂以限制和/或治疗实体肿瘤疾病的药物中的使用。