2-(6-chloro-4-oxoquinazolin-3(4H)-yl)acetic acid | 83798-86-1

• 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-(6-chloro-4-oxoquinazolin-3(4H)-yl)acetic acid
• 英文别名: 6-Chlor-chinazolin-4-on-3-yl-essigsaeure；2-(6-Chloro-4-oxo-3,4-dihydroquinazolin-3-yl)acetic acid；2-(6-chloro-4-oxoquinazolin-3-yl)acetic acid
• CAS: 83798-86-1
• 化学式: C₁₀H₇ClN₂O₃
• mdl: MFCD15730000
• 分子量: 238.63
• InChiKey: YEMHBURPGKVPNM-UHFFFAOYSA-N

物化性质

• 熔点：
  274-276 °C
• 沸点：
  489.5±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-噻吩甲胺 、 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)acetic acid 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 以78.6%的产率得到2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
  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
• 作为产物：
  描述：

  6-Chlor-chinazolin-4-on-3-yl-essigsaeureethylester 以88%的产率得到2-(6-chloro-4-oxoquinazolin-3(4H)-yl)acetic acid
  参考文献：
  名称：

  Chinazolincarbonsäuren。七。米特隆。Ein einfacher Zugang zu（4-Oxo-3,4-dihydrochinazolin-3-yl）-alkansäuren，（4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl）-alkansäurenund deren Estern †

  摘要：

  喹唑啉羧酸。轻松合成（4-Oxo-3,4-dihydroquinazolin-3-yl）-链烷酸，（4-Oxo-3,4-dihydro-1,2,3-3-苯并三嗪-3-基）-链烷酸和他们的酯

  DOI：

  10.1002/hlca.19850680410

文献信息

• Suesse, M.; Johne, S., Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 2, p. 342 - 348
  作者：Suesse, M.、Johne, S.

  DOI：——

  日期：——
• SUESSE, M.;JOHNE, S., J. PRAKT. CHEM., 1984, 326, N 2, 342-348
  作者：SUESSE, M.、JOHNE, S.

  DOI：——

  日期：——
• SUESSE, M.;JOHNE, S., HELV. CHIM. ACTA, 1985, 68, N 4, 892-899
  作者：SUESSE, M.、JOHNE, S.

  DOI：——

  日期：——
• Chinazolincarbonsäuren. VII. Mitteilung. Ein einfacher Zugang zu (4-Oxo-3,4-dihydrochinazolin-3-yl)-alkansäuren, (4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)-alkansäuren und deren Estern
  作者：Manfred Süsse、Siegfried Johne

  DOI：10.1002/hlca.19850680410

  日期：1985.6.26

  Quinazoline Carboxylic Acids. An Easy Route to (4-Oxo-3,4-dihydroquinazolin-3-yl)-alkanoic Acids, (4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)-alkanoic Acids and their Esters

  喹唑啉羧酸。轻松合成（4-Oxo-3,4-dihydroquinazolin-3-yl）-链烷酸，（4-Oxo-3,4-dihydro-1,2,3-3-苯并三嗪-3-基）-链烷酸和他们的酯
• Development of 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis
  作者：Ganesh S. Pedgaonkar、Jonnalagadda Padma Sridevi、Variam Ullas Jeankumar、Shalini Saxena、Parthiban Brindha Devi、Janupally Renuka、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2014.09.028

  日期：2014.10

  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.