2-Thioxo-3-naphth-1'-yl-3,4-dihydrochinazolin-4-on | 22453-82-3

• 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-Thioxo-3-naphth-1'-yl-3,4-dihydrochinazolin-4-on
• 英文别名: 2-thioxo-3-(α-naphthyl)quinazolin-4-one；3--4-oxo-2-thioxo-1.2.3.4-tetrahydro-chinazolin；3-naphthalen-1-yl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one；3-naphthalen-1-yl-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 22453-82-3
• 化学式: C₁₈H₁₂N₂OS
• mdl: MFCD01134714
• 分子量: 304.372
• InChiKey: QDYLLEHZXILBOL-UHFFFAOYSA-N

物化性质

• 熔点：
  320-330 °C
• 沸点：
  504.4±33.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Thioxo-3-naphth-1'-yl-3,4-dihydrochinazolin-4-on 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以63%的产率得到2-hydrazino-3-naphthalen-1-yl-3H-quinazolin-4-one
  参考文献：
  名称：

  Kottke; Kuhmstedt; Griesner, Pharmazie, 1983, vol. 38, # 6, p. 367 - 368

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氨基苯甲酸 、 1-萘异硫氰酸酯 以 乙醇 为溶剂， 反应 5.0h， 以59.1%的产率得到2-Thioxo-3-naphth-1'-yl-3,4-dihydrochinazolin-4-on
  参考文献：
  名称：

  轴向手性喹唑啉-4-酮旋转的能垒

  摘要：

  合成了轴向手性 2-thioxo-3-( o - aryl)-quinazolin-4-ones 和 2-(benzylthio)-3-( o -aryl)-quinazolin-4-ones 及其绕 N 旋转的能垒3- C芳基键通过分离的对映异构体的热外消旋化确定。发现旋转势垒范围从 112.7 到 140.8 kJ/mol，这取决于邻位取代基的大小，并且随着邻位卤素取代基的范德华半径的大小线性增加。尽管具有邻位邻位的 N-C 轴向手性化合物的对映体的分离由于氟原子尺寸小，-氟取代基很少见，我们发现带有邻氟基团的喹唑啉-4-酮的旋转势垒足够高，可以分离对映体。

  DOI：

  10.1016/j.tet.2021.132506

文献信息

• 4(3H)-quinazolinone derivatives and pharmaceutical compositions
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US04861780A1

  公开（公告）日：1989-08-29

  4(3H)-Quinazolinone derivatives of formula (I) are provided. ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, an aryl group, a substituted aryl group, or an aralkyl group; R.sub.2 is a C.sub.1 -C.sub.6 alkylamino group, a phenyl group, a substituted phenyl group, or a 5- or 6-membered heterocyclic group containing one or more N, O or S as a hetero atom or atoms, said heterocyclic group optionally being substituted or fused with a benzene ring; n is 1 or 2; or R.sub.2 represents a geranyl group or a dipyridylmethyl group together with the group --(CH.sub.2).sub.n --; and X is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or a halogen atom, and pharmaceutically acceptable acid addition salts thereof. They are useful as antiulcer agents.

  提供了一种式(I)的4(3H)-喹唑啉酮衍生物。 ##STR1## 其中R1是一个氢原子、C1-C6烷基、芳基、取代芳基或芳烷基；R2是C1-C6烷基氨基、苯基、取代苯基或含有1个或多个N、O或S作为杂原子的5或6元杂环基团，该杂环基团可选择性地被取代或与苯环稠合；n是1或2；或者R2代表与-(CH2)n-基团一起的橙花基或二吡啶甲基；X是氢原子、C1-C6烷基或卤素原子，以及其药学上可接受的酸加成盐。它们作为抗溃疡剂是有用的。
• 4 (3H)-Quinazolinone derivatives, processes for their preparation and pharmaceutical compositions
  申请人：NISSHIN FLOUR MILLING CO., LTD.

  公开号：EP0276825A1

  公开（公告）日：1988-08-03

  4(3H)-Quinazolinone derivatives of formula (I) are provided. wherein R₁ is a hydrogen atom, a C₁-C₆ alkyl group, an aryl group, a substituted aryl group, or an aralkyl group; R₂ is a C₁-C₆ alkylamino group, a phenyl group, a substituted phenyl group, or a 5- or 6-membered heterocyclic group containing one or more N, O or S as a hetero atom or atoms, said heterocyclic group optionally being substituted or fused with a benzene ring; n is 1 or 2; or R₂ represents a geranyl group or a dipyridylmethyl group together with the group -(CH₂)n-; and X is a hydrogen atom, a C₁-C₆ alkyl group or a halogen atom, and pharmaceutically acceptable acid addition salts thereof. They are useful as antiulcer agents.

  提供了式(I)的4(3H)-喹唑啉酮衍生物。 其中 R₁ 是氢原子、C₁-C₆ 烷基、芳基、取代的芳基或芳烷基；R₂ 是 C₁-C₆ 烷胺基、苯基、取代的苯基或含有一个或多个 N、O 或 S 作为杂原子的 5 或 6 元杂环基团，所述杂环基团可选择被苯环取代或与苯环融合；n 是 1 或 2；或 R₂ 代表香叶基团或二吡啶基甲基，连同基团 -(CH₂)n-；以及 X 是氢原子、C₁-C₆ 烷基或卤素原子，及其药学上可接受的酸加成盐。 它们可用作抗溃疡剂。
• CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example
  作者：Ana Castro、María José Jerez、Carmen Gil、Félix Calderón、Teresa Doménech、Arsenio Nueda、Ana Martínez

  DOI：10.1016/j.ejmech.2007.10.027

  日期：2008.7

  Phosphodiesterase (PDE) 7 is a high affinity cAMP-specific PDE whose functional role in T-cells has been the subject of some controversy. Recent findings on tissue distribution, however, support the hypothesis that PDE7 could be a good target for the treatment of airway diseases, T-cell related diseases or central nervous system (CNS) disorders. Therefore, the identification of selective inhibitors targeted against PDE7 enzyme has become an attractive area of research. We report here the first use of the descriptors generated by the CODES program for ligand-based virtual screening. This program codifies molecules from a topological point of view and the generated descriptors are related to the chemical nature of the atoms, the atomic bonds and the connectivity with the rest of the molecule. They are also able to distinguish among stereoisomers. By using this approach, 173 compounds were codified, and their similarity with the reference compound was analysed. Based on the analysis, new potential PDE7 inhibitors have been identified, synthesized and biologically evaluated confirming that CODES descriptors are valid for ligand-based virtual screening and provided new lead compounds for further optimization as potent and selective PDE7 inhibitors. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Jira; Junghanel; Theiss, Pharmazie, 1996, vol. 51, # 5, p. 273 - 279
  作者：Jira、Junghanel、Theiss、Kottke、Besch、Schopplich、Bunke、Leuthold、Beyrich

  DOI：——

  日期：——
• Kottke; Kuhmstedt; Grafe, Pharmazie, 1990, vol. 45, # 4, p. 285 - 286
  作者：Kottke、Kuhmstedt、Grafe、Knoke

  DOI：——

  日期：——