2-(benzo[b]thiophen-2-yl)quinazolin-4(3H)-one | 952737-55-2

• 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-(benzo[b]thiophen-2-yl)quinazolin-4(3H)-one
• 英文别名: 2-(benzo[b]thiophen-2-yl)quinazoline-4(3H)-one；2-(benzo[b]thiophen-3-yl)quinazolin-4(3H)-one；2-(1-benzothien-2-yl)-4(3H)-quinazolinone；2-Benzo[b]thien-2-yl-4(3H)-quinazolinone；2-(1-benzothiophen-2-yl)-3H-quinazolin-4-one
• CAS: 952737-55-2
• 化学式: C₁₆H₁₀N₂OS
• 分子量: 278.334
• InChiKey: VTXKDPZXWHWGLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 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：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzo[b]thiophen-2-yl)quinazolin-4(3H)-one 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 作用下， 反应 12.0h， 以34%的产率得到7,8-diphenyl-5H-benzo[4',5']thieno[2',3':3,4]pyrido[2,1-b]quinazolin-5-one
  参考文献：
  名称：

  The Rh(iii)-catalysed C–H/N–H annulation of 2-thienyl- and 2-phenyl-quinazolin-4(3H)-ones with diphenylacetylene

  摘要：

  用二硫代基/苯基取代的喹唑啉-4(3H)-酮转化为4,5-二苯基-7H-噻吩[2′,3′:3,4]吡啶并[2,1-b]喹唑啉-7-酮或酰胺醇解产物通过与二苯乙炔的Rh(III)催化反应。

  DOI：

  10.1039/d1nj00935d
• 作为产物：
  描述：

  1-苯并噻酚-2-羧醛 在 copper dichloride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 14.0h， 生成 2-(benzo[b]thiophen-2-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  The Rh(iii)-catalysed C–H/N–H annulation of 2-thienyl- and 2-phenyl-quinazolin-4(3H)-ones with diphenylacetylene

  摘要：

  用二硫代基/苯基取代的喹唑啉-4(3H)-酮转化为4,5-二苯基-7H-噻吩[2′,3′:3,4]吡啶并[2,1-b]喹唑啉-7-酮或酰胺醇解产物通过与二苯乙炔的Rh(III)催化反应。

  DOI：

  10.1039/d1nj00935d

文献信息

• Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes
  作者：Muhammad Sharif、Julita Opalach、Peter Langer、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c3ra45765f

  日期：——

  An interesting procedure for the zinc-catalyzed oxidative transformation of ready available 2-aminobenzamide, 2-aminobenzenesulfonamide with benzyl alcohols has been developed. Various quinazolinones and benzothiadiazine 1,1-dioxides were prepared in moderate to good yields under identical conditions. The reactions of both aromatic aldehydes and aliphatic aldehydes with 2-aminobenzamide under catalyst free conditions were described as well. In water media, the products were formed in good yields.

  开发了一种有趣的过程，用于锌催化氧化转化易于获得的2-氨基苯甲酰胺和2-氨基苯磺酰胺与苄醇。在相同条件下，制备了各种喹唉酮和苯并噻二嗪1,1-二氧化物，产率中等至良好。此外，还描述了在无催化剂条件下，2-氨基苯甲酰胺与芳香醛和脂肪醛的反应。在水介质中，产物形成良好产率。
• Catalyst‐free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
  作者：Jiangnan Yang、Zongbo Xie、Zhongsheng Chen、Liang Jin、Qian Li、Zhanggao Le

  DOI：10.1002/jhet.4275

  日期：2021.7

  general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.

  开发了一种通用的无金属氧化环化路线在可见光下合成喹唑啉酮。一系列取代的 2-氨基苯甲酰胺与醛或酮反应，以良好的产率生产所需的喹唑啉酮。最重要的是，该反应不需要过量的氧化剂或高温。
• Therapeutic reactivation of mutant p53 protein by quinazoline derivatives
  作者：Hamish S. Sutherland、In Young Hwang、Elaine S. Marshall、Brent S. Lindsay、William A. Denny、Catherine Gilchrist、Wayne R. Joseph、Debra Greenhalgh、Emma Richardson、Philip Kestell、Angela Ding、Bruce C. Baguley

  DOI：10.1007/s10637-011-9744-z

  日期：2012.10

  Purpose The human tumour suppressor protein p53 is mutated in nearly half of human tumours and most mutant proteins have single amino acid changes. Several drugs including the quinazoline derivative 1 (CP-31398) have been reported to restore p53 activity in mutant cells. The side chain of 1 contains a styryl linkage that compromises its stability and we wished to explore the activity of analogues containing more stable side chains. Methods Reactivation of p53 function was measured by flow cytometry as the ability to potentiate radiation-induced G1-phase cell cycle arrest and by western blotting to determine expression of p21WAF1. DNA binding was measured by competition with ethidium and preliminary pharmacological and xenograft studies were carried out. Results Screening of analogues for potentiation of radiation-induced G1-phase cell cycle arrest using NZOV11, an ovarian tumour cell line containing a p53R248Q mutation, demonstrated that the (2-benzofuranyl)-quinazoline derivative 5 was among the most active of the analogues. Compound 5 showed similar effects in several other p53 mutant human tumour cell lines but not in a p53 null cell line. 5 also potentiated p21WAF1 expression induced by radiation. DNA binding affinity was measured and found to correlate with p53 reactivation activity. Plasma concentrations of 5 in mice were sufficient to suggest in vivo activity and a small induced tumour growth delay (7 days) of NZM4 melanoma xenografts was observed. Conclusion Compound 5 restores p53-like function to a human tumour cells lines expressing a variety of mutant p53 proteins, thus providing a basis for the design of further new drugs.

  目的 在近一半的人类肿瘤中，人类肿瘤抑制蛋白 p53 发生突变，大多数突变蛋白只有一个氨基酸发生变化。据报道，包括喹唑啉衍生物 1（CP-31398）在内的几种药物可恢复突变细胞中 p53 的活性。1 的侧链含有苯乙烯基连接，影响了其稳定性，因此我们希望探索含有更稳定侧链的类似物的活性。方法 通过流式细胞术测量 p53 功能的重激活，即增强辐射诱导的 G1 期细胞周期停滞的能力，并通过 Western 印迹法测定 p21WAF1 的表达。通过乙啶竞争法测定 DNA 结合，并进行了初步的药理学和异种移植研究。结果 使用含有 p53R248Q 突变的卵巢肿瘤细胞系 NZOV11 对类似物进行筛选，以确定其对辐射诱导的 G1 期细胞周期停滞的增效作用，结果表明（2-苯并呋喃基）-喹唑啉衍生物 5 是活性最高的类似物之一。化合物 5 在其他几种 p53 突变的人类肿瘤细胞系中也显示出类似的作用，但在 p53 缺失的细胞系中却没有。5 还能增强辐射诱导的 p21WAF1 的表达。对 DNA 结合亲和力进行了测量，发现它与 p53 的重新激活活性相关。5 在小鼠体内的血浆浓度足以表明其体内活性，并观察到 NZM4 黑色素瘤异种移植物的肿瘤生长略有延迟（7 天）。结论 化合物 5 能使表达多种突变 p53 蛋白的人类肿瘤细胞系恢复类似 p53 的功能，从而为设计进一步的新药物提供了基础。
• 一种可见光诱导合成喹唑啉酮化合物的方法
  申请人：武汉理工大学

  公开号：CN113698358A

  公开（公告）日：2021-11-26

  本发明提供一种可见光诱导合成喹唑啉酮化合物的方法，以邻氨基苯甲酰胺类化合物(I)和醛类化合物(II)为原料，以冰醋酸为溶剂，在紫光照射下反应得到喹唑啉酮化合物(III)。本发明提供的可见光诱导合成喹唑啉酮化合物的方法反应条件温和，后处理操作简便，无需额外添加剂，反应高效，底物适应性广，产物纯度高，绿色环保。
• SUBSTITUTED RING FUSED AZINES AND THEIR USE IN CANCER THERAPY
  申请人：Denny William Alexander

  公开号：US20090318479A1

  公开（公告）日：2009-12-24

  The present invention relates to substituted ring fused azines and methods of using said compounds in treating cancers. More specifically, the present invention relates to the preparation of 4-alkyl-2-(heterocyclic)-azines and their use as cancer agents or drugs for cancer therapy. The compounds of the invention display favourable in vivo and in vitro activity against selected cancers.

  本发明涉及取代环融合吡嗪类化合物及其在治疗癌症中的使用方法。更具体地说，本发明涉及制备4-烷基-2-(杂环)-吡嗪类化合物及其作为癌症治疗药物或药剂的使用。本发明的化合物在体内和体外对选定的癌症表现出良好的活性。