2-(2,3-dihydro-1,4-benzodioxin-6-yl)aminonicotinic acid | 173095-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(2,3-dihydro-1,4-benzodioxin-6-yl)aminonicotinic acid
• 英文别名: 2-((2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)amino)nicotinic acid；2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyridine-3-carboxylic acid
• CAS: 173095-01-7
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: LBJGHELWSGEAKA-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  449.7±45.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,3-dihydro-1,4-benzodioxin-6-yl)aminonicotinic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以72%的产率得到2,3,6,11-tetrahydro-1,4-dioxino[2,3-g]pyrido[2,3-b]quinolin-11-one
  参考文献：
  名称：

  Synthesis and biological evaluation of modified acridines: the effect of N- and O- substituent in the nitrogenated ring on antitumor activity

  摘要：

  A series of new acridines has been prepared by cyclodehydration of N-(2,3-dihydro-1,4-berizodioxin-6-yl)anthranilic acid in acidic media following classical procedures. All these compounds have in common a dioxygenated ring fused to the acridine. The tetracyclic system possesses a linear or angular structure formed by intramolecular cyclisation. The last ring and the substituent of the system modify, in an interesting way, the antitumor activity of acridines. Several of the studied compounds displayed significant cytotoxic activity (inhibition of L 12 10 and HT-29 cell proliferation). The most cytotoxic compound 13a, shows more activity than m-AMSA in inhibiting L1210 and HT-29 cell proliferation and this compound has been selected as a development candidate for further evaluation. The activity results also indicate that the new 11-O-substituted compounds are of considerable interest with high levels of cytotoxic activity. The angular or non-linear dioxinoacridine 10 was equiactive with the linear structure 7. Pentacyclic analogues (14 and 15) were more cytotoxic than the tetracyclic compounds (up to twofold). (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.006
• 作为产物：
  描述：

  2-氯烟酸 、 6-氨基-1,4-苯并二氧杂环 在 铜 作用下， 以 xylene 为溶剂， 反应 24.0h， 以70%的产率得到2-(2,3-dihydro-1,4-benzodioxin-6-yl)aminonicotinic acid
  参考文献：
  名称：

  Mefetah, Hafid; Brouant, Pierre; Galy, Anne-Marie, Medicinal Chemistry Research, 1995, vol. 5, # 7, p. 522 - 533

  摘要：

  DOI：

文献信息

• RING-FUSED 2-PYRIDONE DERIVATIVES AND HERBICIDES
  申请人：Kumiai Chemical Industry CO., LTD.

  公开号：EP2394995A1

  公开（公告）日：2011-12-14

  Provided are 2-pyridone derivatives which have excellent herbicidal activity and exhibit high safety to useful crops and so on; salts thereof; and herbicides containing same. In more detail, 2-pyridone derivatives represented by general formula [I] or agrochemically acceptable salts thereof, and herbicides containing these compounds are provided. In general formula [I], X1 is an oxygen atom or a sulfur atom; X2, X3, and X4 are each CH or N(O)m; m is an integer of 0 or 1; R1 is a hydrogen atom, a C1-12 alkyl group, or the like; R2 is a halogen atom, a cyano group, or the like; n is an integer of 0 to 4; R3 is a hydroxyl group, a halogen atom, or the like; A1 is C(R11R12); A2 is C(R13R14) or C=O; A3 is C(R15R16); and R11, R12, R13, R14, R15, and R16 are each independently a hydrogen atom or a C1-6 alkyl group.

  本发明提供了具有优异除草活性并对有用作物等表现出高度安全性的 2-吡啶酮衍生物；其盐类；以及含有这些衍生物的除草剂。更详细地说，本发明提供了由通式[I]表示的 2-吡啶酮衍生物或其农用化学品可接受的盐，以及含有这些化合物的除草剂。在通式[I]中，X1 是氧原子或硫原子；X2、X3 和 X4 分别是 CH 或 N(O)m；m 是 0 或 1 的整数；R1 是氢原子、C1-12 烷基或类似物；R2 是卤素原子、氰基或类似物；n 是 0 至 4 的整数；R3 是羟基、卤素原子或类似物；A1 是 C(R11R12)；A2 是 C(R13R14) 或 C=O；A3 是 C(R15R16)；以及 R11、R12、R13、R14、R15 和 R16 各自独立地是氢原子或 C1-6 烷基。
• Mefetah, Hafid; Brouant, Pierre; Galy, Anne-Marie, Medicinal Chemistry Research, 1995, vol. 5, # 7, p. 522 - 533
  作者：Mefetah, Hafid、Brouant, Pierre、Galy, Anne-Marie、Galy, Jean-Pierre、Barbe, Jacques

  DOI：——

  日期：——
• Synthesis and biological evaluation of modified acridines: the effect of N- and O- substituent in the nitrogenated ring on antitumor activity
  作者：Isabel Sánchez、Rosa Reches、Daniel Henry Caignard、Pierre Renard、Maria Dolors Pujol

  DOI：10.1016/j.ejmech.2005.11.006

  日期：2006.3

  A series of new acridines has been prepared by cyclodehydration of N-(2,3-dihydro-1,4-berizodioxin-6-yl)anthranilic acid in acidic media following classical procedures. All these compounds have in common a dioxygenated ring fused to the acridine. The tetracyclic system possesses a linear or angular structure formed by intramolecular cyclisation. The last ring and the substituent of the system modify, in an interesting way, the antitumor activity of acridines. Several of the studied compounds displayed significant cytotoxic activity (inhibition of L 12 10 and HT-29 cell proliferation). The most cytotoxic compound 13a, shows more activity than m-AMSA in inhibiting L1210 and HT-29 cell proliferation and this compound has been selected as a development candidate for further evaluation. The activity results also indicate that the new 11-O-substituted compounds are of considerable interest with high levels of cytotoxic activity. The angular or non-linear dioxinoacridine 10 was equiactive with the linear structure 7. Pentacyclic analogues (14 and 15) were more cytotoxic than the tetracyclic compounds (up to twofold). (c) 2006 Elsevier SAS. All rights reserved.