3-benzyl-2,3-dihydro-6-nitro-2-thioxoquinazolin-4(1H)-one

• 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: 3-benzyl-2,3-dihydro-6-nitro-2-thioxoquinazolin-4(1H)-one
• 英文别名: 3-benzyl-6-nitro-2-thioxo-2,3-dihydroquinazolin-4(1H)-one；3-benzyl-2-mercapto-6-nitroquinazolin-4(3H)-one；3-benzyl-6-nitro-2-sulfanylidene-1H-quinazolin-4-one
• 化学式: C₁₅H₁₁N₃O₃S
• 分子量: 313.337
• InChiKey: CAFCJNRLHXPRGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-2,3-dihydro-6-nitro-2-thioxoquinazolin-4(1H)-one 以 甲醇 为溶剂， 反应 10.0h， 以78%的产率得到3-benzyl-6-nitro-2,4-(1H,3H)-quinazolinedione
  参考文献：
  名称：

  2-硫代-2,3-二氢喹唑啉-4（1H）-酮显着转化为相应的喹唑啉-2,4（1H，3H）-二酮：光谱分析和X射线晶体学

  摘要：

  一个简单的和有效的新的合成方法，得到3-取代的喹唑啉-2,4-二酮9 -通过3-取代的-2-硫代喹唑啉-4-酮反应16 1 - 8与温和的条件下氨基钠提出。新合成的化合物的结构通过红外光谱，紫外可见光谱，核磁共振和单晶X射线晶体学分析确定。6-甲基-3-苯基喹唑啉-2,4（1H，3H）-二酮的晶体结构（11）[C 15 H 12 N 2 O 2：MF = 252.27，三斜晶系，P-1，a  = 7.8495（13 ）Å，b  = 12.456（2）Å，c = 13.350（2）埃，α  = 103.322（3）°，β  = 90.002（3）°，γ  = 102.671（4）°，V = 1237.5（3）3，Ž  = 4，- [R  = 0.0592，WR =确定为0.1699，S  ＝ 1.039]。在该晶胞中，发现化合物11的两个相同构象异构体通过分子内氢键连接，这是这两个独立分子的有利发生原因。

  DOI：

  10.1155/2021/6612177
• 作为产物：
  描述：

  异硫氰酸苯甲酯 、 2-氨基-5-硝基苯甲酸 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 3-benzyl-2,3-dihydro-6-nitro-2-thioxoquinazolin-4(1H)-one
  参考文献：
  名称：

  喹唑啉-4-酮的功能化第2部分：2-氨基-3、4、5或6-硝基苯甲酸与三苯基膦硫氰酸酯，异硫氰酸烷基酯的反应性以及进一步的衍生化反应

  摘要：

  使2-氨基-3、4、5或6-硝基苯甲酸与PPh 3（SCN）2和异硫氰酸烷基酯反应，得到5、6、7或8-硝基-2-硫代-3-4取代的喹唑啉-4分别为一个。发现硝基的位置对反应的结果有重大影响。同样，还发现8-取代-2-甲硫基喹唑啉-4-酮中第8位的取代基（NO 2，NH 2，NH（C substituentO）CH 3）的性质也会显着影响其对吗啉的反应性。还测试了选择的产品的体外抗菌活性，但是观察到很少的活性。

  DOI：

  10.1002/jhet.2235

文献信息

• Non-classical antifolates. Part 2: Synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones
  作者：Fatmah A.M. Al-Omary、Laila A. Abou-zeid、Mahmoud N. Nagi、El-Sayed E. Habib、Alaa A.-M. Abdel-Aziz、Adel S. El-Azab、Sami G. Abdel-Hamide、Mohamed A. Al-Omar、Abdulrahman M. Al-Obaid、Hussein I. El-Subbagh

  DOI：10.1016/j.bmc.2010.03.019

  日期：2010.4

  Compounds 34 and 36 showed antitumor activity at GI50 (MG-MID) concentrations of 11.2, and 24.2 μM, respectively. Molecular modeling study including flexible alignment; electrostatic, hydrophobic mappings; and pharmacophore prediction were performed. A main featured pharmacophore model was developed which justifies the importance of the main pharmacophoric groups as well as of their relative distances.

  设计，合成和评估了一系列新的2，6-取代的喹唑啉-4-酮，并对其体外DHFR抑制，抗菌和抗肿瘤活性进行了评估。化合物22，33-37，39-43，和45被证明是活性DHFR抑制剂与IC 50范围0.4-1.0微米。化合物18显示出与已知抗生素庆大霉素相当的广谱抗菌活性。化合物34和36在GI 50时显示抗肿瘤活性（MG-MID）浓度分别为11.2和24.2μM。分子建模研究，包括灵活的比对；静电，疏水图谱；和药效团预测进行。开发了一个主要的药效基团模型，该模型证明了主要药效基团及其相对距离的重要性。关于喹唑啉核的π系统的取代模式和空间考虑被证明对生物活性至关重要。
• Quinazoline–sulfonamides with potent inhibitory activity against the α-carbonic anhydrase from Vibrio cholerae
  作者：Ahmed M. Alafeefy、Mariangela Ceruso、Abdul-Malek S. Al-Tamimi、Sonia Del Prete、Clemente Capasso、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2014.08.015

  日期：2014.10

  Thirteen novel sulfonamide derivatives incorporating the quinazoline scaffold were synthesized by simple, eco-friendly procedures. These compounds were tested for their ability to inhibit the alpha-carbonic anhydrases (CA, EC 4.2.1.1) from Vibrio cholerae (VchCA) as well as the human alpha-CA isoforms, hCA I and hCA II. Nine compounds were highly effective, nanomolar inhibitors of the pathogenic enzyme VchCA. Three of them were also highly effective sub-nanomolar inhibitors of the cytosolic isoform II. The best VchCA inhibitor had a K-I of 2.7 nM. Many of these developed compounds showed high selectivity for inhibition of the bacterial over the mammalian CA isoforms, with one compound possessing selectivity ratios as high as 97.9 against hCA I and 9.7 against hCA II. Compound 9d was another highly effective VchCA inhibitor presenting a selectivity ratio of 99.1 and 8.1 against hCA I and hCA II, respectively. These results suggest that sulfonamides with quinazoline backbone could be considered suitable tools to better understand the role of bacterial CAs in pathogenesis. (C) 2014 Elsevier Ltd. All rights reserved.
• Novel 4(3H)-quinazolinone analogs: synthesis and anticonvulsant activity
  作者：Adel S. El-Azab、Sami G. Abdel-Hamide、Mohamed M. Sayed-Ahmed、Ghada S. Hassan、Tariq M. El-Hadiyah、Othman A. Al-Shabanah、Omar A. Al-Deeb、Hussein I. El-Subbagh

  DOI：10.1007/s00044-012-0280-y

  日期：2013.6

  A new series of quinazoline analogs was designed, synthesized, and evaluated for their anticonvulsant activity. Compounds 6, 12, 21, 36, 37, and 38 showed 70-100 % protection against PTZ-induced seizures acting as GABA(A) receptor agonists. Compound N-(3,4,5,6-tetrachloro-phthalimido)-2-[(3-phenyl-4-oxo-6-methyl-3H-quinazolin-2-yl)-thio]acetamide (12) representing the moderate active compounds and 2-[6-iodo-4-oxo-2-(thiophen-2-yl)-quinazolin-3(4H)-yl]-isoindoline-1,3-dione (38) representing the remarkably active compounds in this stud, showed ED50 values of 457 and 251 mg/kg; TD50 values of 562 and 447 mg/kg; PI values of 1.22 and 1.78, LD50 values of 1,288 and 1,380 mg/kg, and TI values of 2.82 and 5.50, respectively. Compound 38 proved to be almost twofold more active than the standard drug sodium valproate.
• Remarkable Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones into the Corresponding Quinazoline-2,4(1H,3H)-diones: Spectroscopic Analysis and X-Ray Crystallography
  作者：Adel S. El-Azab、Nasr Y. Khalil、Alaa A.-M. Abdel-Aziz

  DOI：10.1155/2021/6612177

  日期：2021.4.2

  analysis. The crystal structure of 6-methyl-3-phenylquinazoline-2,4(1H,3H)-dione (11) [C15H12N2O2: MF = 252.27, triclinic, P-1, a = 7.8495 (13) Å, b = 12.456 (2) Å, c = 13.350 (2) Å, α = 103.322 (3)°, β = 90.002 (3)°, γ = 102.671 (4)°, V = 1237.5 (3) Å3, Z = 4, R = 0.0592, wR = 0.1699, S = 1.039] was determined. In the crystal cell, two identical conformers of compound 11 were found connected by intramolecular

  一个简单的和有效的新的合成方法，得到3-取代的喹唑啉-2,4-二酮9 -通过3-取代的-2-硫代喹唑啉-4-酮反应16 1 - 8与温和的条件下氨基钠提出。新合成的化合物的结构通过红外光谱，紫外可见光谱，核磁共振和单晶X射线晶体学分析确定。6-甲基-3-苯基喹唑啉-2,4（1H，3H）-二酮的晶体结构（11）[C 15 H 12 N 2 O 2：MF = 252.27，三斜晶系，P-1，a  = 7.8495（13 ）Å，b  = 12.456（2）Å，c = 13.350（2）埃，α  = 103.322（3）°，β  = 90.002（3）°，γ  = 102.671（4）°，V = 1237.5（3）3，Ž  = 4，- [R  = 0.0592，WR =确定为0.1699，S  ＝ 1.039]。在该晶胞中，发现化合物11的两个相同构象异构体通过分子内氢键连接，这是这两个独立分子的有利发生原因。
• Functionalization of Quinazolin-4-Ones Part 2^#: Reactivity of 2-Amino-3, 4, 5, or 6-Nitrobenzoic Acids with Triphenylphosphine Thiocyanate, Alkyl Isothiocyanates, and Further Derivatization Reactions
  作者：Jacob T. Heppell、Jasim M. A. Al-Rawi

  DOI：10.1002/jhet.2235

  日期：2015.9

  2‐amino‐3, 4, 5, or 6‐nitrobenzoic acids were reacted with PPh3(SCN)2 and alkyl isothiocyanates to give 5, 6, 7, or 8‐nitro‐2‐thioxo‐3‐substituted quinazolin‐4‐ones, respectively. The position of the nitro group was found to have significant influence on the outcome of the reactions. Similarly, the nature of the substituent at position 8 (NO2, NH2, NH(C═O)CH3) in 8‐substituted‐2‐methylthio quinazolin‐4‐ones

  使2-氨基-3、4、5或6-硝基苯甲酸与PPh 3（SCN）2和异硫氰酸烷基酯反应，得到5、6、7或8-硝基-2-硫代-3-4取代的喹唑啉-4分别为一个。发现硝基的位置对反应的结果有重大影响。同样，还发现8-取代-2-甲硫基喹唑啉-4-酮中第8位的取代基（NO 2，NH 2，NH（C substituentO）CH 3）的性质也会显着影响其对吗啉的反应性。还测试了选择的产品的体外抗菌活性，但是观察到很少的活性。