3-amino-2-(methylthio)quinazolin-4(3H)-one | 261509-54-0

• 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: 3-amino-2-(methylthio)quinazolin-4(3H)-one
• 英文别名: 3-amino-2-methylsulfanylquinazolin-4-one
• CAS: 261509-54-0
• 化学式: C₉H₉N₃OS
• mdl: MFCD00463043
• 分子量: 207.256
• InChiKey: RRIRPPABZOKWCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-159 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  395.6±25.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-2-(methylthio)quinazolin-4(3H)-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 3-氨基-2-肼基喹唑啉-4-酮
  参考文献：
  名称：

  Majahid, Abdul Khadar; Kalyane; Shivkumar, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 129 - 132

  摘要：

  DOI：
• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 3-amino-2-(methylthio)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones

  摘要：

  A series of 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones have been synthesized by the cyclocondensation of 3-amino-2-benzylamino-3H-quinazolin-4-one with a variety of one-carbon donors. The starting material 3-amino-2-benzyl-amino- 3H-quinazolin-4-one was synthesized from methyl anthranilate by a novel innovative route. The title compounds were evaluated for their in vivo antihypertensive activity using spontaneously hypertensive rats (SHR). While all the test compounds exhibited significant antihypertensive activity, 3-benzyl-2-methyl-3H-[1,2,4]triazolo[5,1-b] quinazolin-9-one exhibited antihypertensive activity more than the reference standard prazocin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.007

文献信息

• Synthesis of some quinazolinones inspired from the natural alkaloid L<i>-</i>norephedrine as EGFR inhibitors and radiosensitizers
  作者：Mostafa M. Ghorab、Maged S. Abdel-Kader、Ali S. Alqahtani、Aiten M. Soliman

  DOI：10.1080/14756366.2020.1854243

  日期：2021.1.1

  Abstract A set of quinazolinones synthesized by the aid of L-norephedrine was assembled to generate novel analogues as potential anticancer and radiosensitizing agents. The new compounds were evaluated for their cytotoxic activity against MDA-MB-231, MCF-7, HepG-2, HCT-116 cancer cell lines and EGFR inhibitory activity. The most active compounds 5 and 6 were screened against MCF-10A normal cell line

  摘要 在 L-去甲麻黄碱的帮助下合成了一组喹唑啉酮类化合物，以产生新的类似物作为潜在的抗癌剂和放射增敏剂。评估了这些新化合物对 MDA-MB-231、MCF-7、HepG-2、HCT-116 癌细胞系的细胞毒活性和 EGFR 抑制活性。针对 MCF-10A 正常细胞系筛选出最活跃的化合物5和6 ，并显示出较低的毒性作用。他们证明了它们对 MDA-MB-231 乳腺癌细胞系具有高选择性的相对安全性。对5和6的放射增敏活性的测量表明，它们可以在暴露于单剂量 8 Gy 伽马辐射后使肿瘤细胞敏感。化合物5能够诱导细胞凋亡并将细胞周期停滞在G2-M期。在 EGFR 的活性位点进行5和6的分子对接以深入了解与关键氨基酸的结合相互作用。
• ISATIN DERIVATIVES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE THEREOF
  申请人：Horne David A.

  公开号：US20130225637A1

  公开（公告）日：2013-08-29

  One aspect of the invention relates to novel isatin derivative compounds and the pharmaceutical composition thereof. Another aspect of the invention relates to methods of using the isatin derivative compounds disclosed herein and the pharmaceutical compositions thereof. In certain embodiments, the method is used to treat a cancer or a tumor in a subject including, without limitation, prostate cancer, melanoma, pancreatic cancer, ovarian cancer, and lymphoma. In certain embodiment, the method is used to treat a condition in a subject that can be regulated by the activation of one or more proteins such as EGFR, Erk1/2, Her2/Neu, Jak2, Src, Stat3, Akt, Cyclin B1, and Cdc25C. In certain embodiment, the method is used to treat a condition in a subject that can be regulated by the disruption of microtubule formations.

  该发明的一个方面涉及新型异喹啉衍生物化合物及其药物组合物。该发明的另一个方面涉及使用本文披露的异喹啉衍生物化合物和其药物组合物的方法。在某些实施例中，该方法用于治疗受试者中的癌症或肿瘤，包括但不限于前列腺癌、黑色素瘤、胰腺癌、卵巢癌和淋巴瘤。在某些实施例中，该方法用于治疗受试者中可以通过激活EGFR、Erk1/2、Her2/Neu、Jak2、Src、Stat3、Akt、Cyclin B1和Cdc25C等一个或多个蛋白质来调节的疾病。在某些实施例中，该方法用于治疗受试者中可以通过破坏微管形成来调节的疾病。
• Synthesis, Analgesic, Anti-inflammatory and Antibacterial Activities of some Novel 2-Methylthio-3-Substituted Quinazolin-4-(3H)-ones
  作者：Veerachamy Alagarsamy、Ramadoss Rajesh、Meena Ramaseshu、Sukumaran Vijaykumar、Kona Venkat Ramseshu、Thirumoorthy Duraianandakumar

  DOI：10.1248/bpb.27.652

  日期：——

  variety of novel 2-methylthio-3-substituted quinazolin-4-(3H)-ones have been synthesized by reacting (2-methylthio-4-oxo-3H-quinazolin-3-yl)dithiocarbamic acid methyl ester with a variety of amines, the starting material dithiocarbamate was synthesized from methylanthranilate. The title compounds were investigated for analgesic, anti-inflammatory and antibacterial activities. While the test compounds exhibited

  通过使（2-甲硫基-4-氧代-3H-喹唑啉-3-基）二硫代氨基甲酸甲酯与多种二甲基氨基甲酸酯反应合成了多种新颖的2-甲硫基-3-取代的喹唑啉-4-（3H）-。胺，从二邻氨基苯甲酸甲酯合成起始原料二硫代氨基甲酸酯。研究了标题化合物的镇痛，抗炎和抗菌活性。尽管受试化合物显示出显着的活性，但化合物A1，A2，A3和A4的镇痛活性更高，而化合物A4的抗炎活性比参考双氯芬酸钠更高。
• Synthesis, Analgesic and Anti-inflammatory Activities of Some Novel 2,3-Disubstituted Quinazolin-4(3H)-ones.
  作者：Veerachamy Alagarsamy、Veluchamy Muthukumar、Nagendran Pavalarani、Poongavanam Vasanthanathan、Rajappan Revathi

  DOI：10.1248/bpb.26.557

  日期：——

  A series of novel 2-benzylamino-3-substituted quinazolin-4(3H)-ones have been synthesized by treating 3-amino-2-benzylamino quinazolin-4(3H)-one, with different aldehydes and ketones. The starting material 3-amino-2-benzylamino quinazolin-4(3H)-one was synthesized by nucleophilic substitution of thiomethyl group of 3-amino-2-methylthio quinazolin-4(3H)-one by benzylamine. The title compounds were investigated for analgesic and anti-inflammatory activities. All the test compounds exhibited significant analgesic activity, whereas the compound III is equipotent with diclofenac sodium. The compounds I, II and III showed more potent anti-inflammatory activity than diclofenac sodium.

  通过用不同的醛和酮处理3-氨基-2-苄氨基喹唑啉-4(3H)-酮，合成了一系列新型2-苄氨基-3-取代的喹唑啉-4(3H)-酮。以3-氨基-2-甲硫基喹唑啉-4(3H)-酮的硫甲基被苄胺亲核取代，合成了起始原料3-氨基-2-苄氨基喹唑啉-4(3H)-酮。研究了标题化合物的镇痛和抗炎活性。所有测试化合物均表现出显着的镇痛活性，而化合物III与双氯芬酸钠等效。化合物I、II和III显示出比双氯芬酸钠更有效的抗炎活性。
• Pyrimidine derivatives
  申请人：Sato Michitaka

  公开号：US20070197551A1

  公开（公告）日：2007-08-23

  This invention provides pyrimidine derivatives represented by a formula, in the formula, ring A stands for carbocyclic group or heterocyclic group, X 1 stands for hydrogen, lower alkyl, amino, etc., X 2 stands for hydrogen or lower alkyl, Y stands for a direct bond or sulfur or nitrogen, n stands for an integer of 0-4, and Ar stands for a group of the following formula, or a salt thereof, which concurrently exhibit 5-HT 1A agonistic activity and 5-HT 3 antagonistic activity and are useful for therapy and treatments of diseases such as IBS. The invention furthermore provides a therapeutic method of IBS, characterized by having 5-HT 1A agonistic activity and 5-HT 3 antagonistic activity work simultaneously and cooperatively in vivo, which comprises either administering 5-HT 3 antagonistic agent which concurrently exhibits 5-HT 1A agonistic activity, or administering 5-HT 1A agonistic agent and 5-HT 3 antagonistic agent simultaneously, in sequence or at an interval.

  本发明提供了由下式表示的嘧啶衍生物，其中，环A代表碳环基团或杂环基团，X1代表氢、低碳基、氨基等，X2代表氢或低碳基，Y代表直接键或硫或氮，n代表0-4的整数，Ar代表以下式的基团，或其盐，同时表现出5-HT1A激动活性和5-HT3拮抗活性，并且对治疗诸如肠易激综合征等疾病有用。本发明进一步提供了一种IBS治疗方法，其特征在于在体内同时和协同地发挥5-HT1A激动活性和5-HT3拮抗活性，包括给予同时表现出5-HT1A激动活性和5-HT3拮抗活性的5-HT3拮抗剂，或同时给予5-HT1A激动剂和5-HT3拮抗剂，按顺序或间隔给予。