2-(2-methyl-4-oxoquinazolin-3(4H)-yl) acetic acid | 50844-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(2-methyl-4-oxoquinazolin-3(4H)-yl) acetic acid
• 英文别名: (2-Methyl-4-oxo-4H-quinazolin-3-yl)-acetic acid；2-(2-methyl-4-oxoquinazolin-3-yl)acetic acid
• CAS: 50844-81-0
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD00197325
• 分子量: 218.212
• InChiKey: NIRPYXSTQBPOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-4-oxoquinazolin-3(4H)-yl) acetic acid 在 氯化亚砜 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-(2-甲基-4-氧喹唑啉-3-基)乙酰肼
  参考文献：
  名称：

  Panda; Srinivas; Rao, M.E. Bhanoji, Journal of the Indian Chemical Society, 2002, vol. 79, # 9, p. 770 - 771

  摘要：

  DOI：
• 作为产物：
  描述：

  邻乙酰胺苯甲酸內酯 在 caesium carbonate 、 formamide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-(2-methyl-4-oxoquinazolin-3(4H)-yl) acetic acid
  参考文献：
  名称：

  Development of 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis

  摘要：

  InhA, the enoyl acyl carrier protein reductase of Mycobacterium tuberculosis (MTB) is an attractive target for developing novel anti-tubercular agents. Twenty eight 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives were synthesized and evaluated for their in vitro MTB InhA inhibition. Compounds were further evaluated for their in vitro activity against drug sensitive and resistant MTB strains and cytotoxicity against RAW 264.7 cell line. Compounds were docked at the active site of InhA to understand their binding mode and differential scanning fluorimetry was performed to ascertain their protein interaction and stability. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.028

文献信息

• The art of design in azlactone–benzoxazinone chemistry, docking studies and
  作者：Shadi Dadkhah、Mahla Malekzadeh、Farshid Hassanzadeh、Ghadamali Khodarahmi、Parvin Asadi、Mahboubeh Rostami

  DOI：10.1071/ch21275

  日期：——

  In this study, by combining azlactone–benzoxazinone chemistry, we synthesized new hybrid compounds and evaluated the in vitro cytotoxicity on the breast cancer cell line. The desired compounds were synthesized using green and straightforward chemical reactions on azlactone and benzoxazinone structures through simple ring closure and nucleophilic ring-opening reactions. Preliminary in vitro cytotoxic results on the MCF-7 breast cancer cell line showed that the synthesized compounds have excellent anticancer activity with interestingly low inhibitory concentrations (IC50s in the range of 8–20 mM). Fortunately, our structures simultaneously had low toxicity on the normal HUVEC cell line. Finally, molecular docking studies were performed on the EGFR enzyme as one of the active signaling pathways in cancer cells for the best cytotoxic candidates. In this regard, the alignment of the docking and cytotoxicity results was interesting. In conclusion, these potential cytotoxic compounds could be considered in further studies.

  在本研究中，我们结合氮内酯-苯并恶嗪酮化学，合成了新的杂化化合物，并评估了其对乳腺癌细胞系的体外细胞毒性。通过简单的闭环反应和亲核开环反应，我们利用氮内酯和苯并恶嗪酮结构的绿色直接化学反应合成了所需的化合物。对 MCF-7 乳腺癌细胞系的初步体外细胞毒性结果表明，合成的化合物具有出色的抗癌活性，而且抑制浓度（IC50 在 8-20 mM 之间）非常低。幸运的是，我们的化合物结构同时对正常的 HUVEC 细胞株具有低毒性。最后，我们对表皮生长因子受体（EGFR）酶进行了分子对接研究，该酶是癌细胞中活跃的信号传导途径之一，可寻找最佳细胞毒性候选物。在这方面，对接和细胞毒性结果的一致性非常有趣。总之，这些潜在的细胞毒性化合物可在进一步的研究中加以考虑。
• Ruthenium(II) complexes with 2-methyl-3-substituted (3H)-quinazolin-4-ones
  作者：K.Laxma Reddy、P. Lingaiah、K.Veera Reddy

  DOI：10.1016/s0277-5387(00)84550-7

  日期：1986.1

  complexes of some polydentate ON, OO and ONO donors in the form of 2-methyl-3-substituted (3H)-quinazolin-4-ones have been synthesized and studied. The reaction between RuCl2(DMSO)4 and the uninegative bidentate ligands yielded complexes of the type Ru(DMSO)2(OO)2 (OO = MHQ, PHQ, MHEQ, MHPQ or MCMQ), displacing only two DMSO groups along with chlorides, whereas the neutral bidentate ligands gave

  合成了一些多齿ON，OO和ONO供体的钌（II）配合物，它们以2-甲基-3-取代的（3 H）-喹唑啉-4-酮的形式存在，并且研究过。RuCl 2（DMSO）4与非负二齿配体之间的反应产生Ru（DMSO）2（OO）2类型的配合物（OO= MHQ，PHQ，MHEQ，MHPQ或MCMQ），仅取代了两个DMSO基团以及氯化物，而中性双齿配体给出RuCl 2（ON）2（ON= MAQ，PAQ，MANQ，PANQ，MAAQ，MAPQ，MPQ或PPQ），取代了所有DMSO基团。然而，具有O = N = O供体的单负性齿状配体（MHAQ）生成了钌（II）的双螯合物。
• AN ANTIMALARIAL ALKALOID FROM HYDRANGEA. XV. SYNTHESIS OF 5-, 6-, 7-, AND 8-DERIVATIVES WITH TWO IDENTICAL SUBSTITUENTS
  作者：B. R. BAKER、ROBERT E. SCHAUB、JOSEPH P. JOSEPH、FRANCIS J. McEVOY、JAMES H. WILLIAMS

  DOI：10.1021/jo01135a015

  日期：1952.1
• Prabhakar, B; Lingaiah, P; Reddy, K Laxma, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1991, vol. 30, # 10, p. 904 - 907
  作者：Prabhakar, B、Lingaiah, P、Reddy, K Laxma

  DOI：——

  日期：——
• ESR and other spectral studies on copper(II) complexes with 2,3-disubstituted quinazoline-(3H)-4-ones
  作者：B. Prabhakar、P. Lingaiah、K.Laxma Reddy

  DOI：10.1016/s0277-5387(00)81345-5

  日期：1990.1