4-morpholin-4-yl-2-phenylquinazoline | 307544-21-4

• 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: 4-morpholin-4-yl-2-phenylquinazoline
• 英文别名: 4-(2-phenylquinazolin-4-yl)morpholine
• CAS: 307544-21-4
• 化学式: C₁₈H₁₇N₃O
• 分子量: 291.352
• InChiKey: LELHZGOHVCQBJP-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  408.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-morpholin-4-yl-2-phenylquinazoline 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 生成 4-morpholin-4-yl-2-phenylquinazoline hydrochloride
  参考文献：
  名称：

  Design and synthesis of 4-amino-2-phenylquinazolines as novel topoisomerase I inhibitors with molecular modeling

  摘要：

  4-Amino-2-phenylquinazolines 7 were designed as bioisosteres of 3-arylisoquinolinamines 6 that were energy minimized to provide stable conformers. Interestingly, the 2-phenyl ring of 4-amino-2-phenylquinazolines was parallel to the quinazoline ring and improved their DNA intercalation ability in the DNA-topo I complex. Among the synthesized 4-amino group-substituted analogs, 4-cyclohexylamino-2-phenylquinazoline 7h exhibited potent topo I inhibitory activity and strong cytotoxicity. Interestingly, consistency was observed between the cytotoxicities and topo I activities in these quinazoline analogs, suggesting that the target of 4-amino-2-phenylquinazolines is limited to topo I. Molecular docking studies were performed with the Surflex-Dock program to afford the ideal interaction mode of the compound into the binding site of the DNA-topo I complex in order to clarify the topo I activity of 7h. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.012
• 作为产物：
  描述：

  2-氨基-2-苯基乙酸 在 碘 、 三氟乙酸 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 26.0h， 生成 4-morpholin-4-yl-2-phenylquinazoline
  参考文献：
  名称：

  通过 I2/DMSO 促进的 α-氨基酸氧化脱羧和随后的氧化环化反应生成喹唑啉酮衍生物的有效途径

  摘要：

  揭示了一种有效且直接的策略，通过分子碘从商业廉价的 2-氨基苯甲酰胺和各种氨基酸合成各种喹唑啉酮衍生物，促进 α-氨基酸的氧化脱羧，然后进行氧化环化反应。操作简单、产量一致、官能团耐受性和可持续性是该反应的其他值得注意的特征。采用目前的策略可以方便地制备大量喹唑啉酮衍生物。在相同的反应条件下合成其他相关的杂芳烃，如苯并恶唑和苯并噻唑衍生物，拓宽了该方法的范围。

  DOI：

  10.1055/a-2065-3169

文献信息

• A Convenient Route to Biologically Important Quinazolines Using<i>N</i>-Arylamino-1,3-diazabuta-1,3-dienes
  作者：M. P. Mahajan、Vipan Kumar、Gaurav Bhargava、Promita D. Dey

  DOI：10.1055/s-2005-918419

  日期：——

  A potential and convenient protocol for the synthesis of 4-arylquinazolines and 4-aminoquinazolines by electrocyclisation of N-arylamino-1,3-diazabuta-1,3-dienes is described.

  描述了通过 N-arylamino-1,3-diazabuta-1,3-dienes 的电环化合成 4-arylquinazolines 和 4-aminoquinazolines 的潜在且方便的协议。
• N-heterocyclic carbene-Pd(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of 2-chloro-4-aminoquinazolines with arylboronic acids
  作者：Zhen Bao、Zhi-Yuan Zhou、Ye-Ting Mao、Li-Xiong Shao

  DOI：10.1016/j.tet.2020.131548

  日期：2020.10

  The Suzuki-Miyaura coupling between 2-chloro-4-aminoquinazolines and arylboronic acids catalyzed by the well-defined N-heterocyclic carbene-PdCl2-1-methylimidazole complex was performed at room temperature, giving the desired products in good to high yields. Through this methodology, a variety of 2-aryl-4-aminoquinazoline derivatives with potential pharmaceutical activities can be achieved under mild reaction conditions. (C) 2020 Elsevier Ltd. All rights reserved.
• Compositions And Methods For Reducing Cancer And Inflammation
  申请人：Varner Judith A.

  公开号：US20100278837A1

  公开（公告）日：2010-11-04

  This invention relates to the discovery of the convergence of diverse receptors and signaling pathways on the PI3gamma dependent activation of VLA4 (integrin a4b1). In particular, the invention relates to the role of myeloid cells in tumor inflammation and metastasis. The invention provides methods for inhibiting cancer in a subject comprising administering to a subject having cancer that comprises endothelial cells a therapeutically effective amount of a PI-3-kinase gamma inhibitor that reduces at least one of (a) adhesion of myeloid cells to the endothelial cells, (b) migration of myeloid cells into the cancer, (c) growth of the cancer, (d) activation of integrin a4b1 that is comprised on the myeloid cells, and (e) clustering of integrin a4b1 that is comprised on the myeloid cells.
• Design and synthesis of 4-amino-2-phenylquinazolines as novel topoisomerase I inhibitors with molecular modeling
  作者：Thanh Nguyen Le、Su Hui Yang、Daulat Bikram Khadka、Hue Thi My Van、Suk Hee Cho、Youngjoo Kwon、Eung-Seok Lee、Kyung-Tae Lee、Won-Jea Cho

  DOI：10.1016/j.bmc.2011.05.012

  日期：2011.7

  4-Amino-2-phenylquinazolines 7 were designed as bioisosteres of 3-arylisoquinolinamines 6 that were energy minimized to provide stable conformers. Interestingly, the 2-phenyl ring of 4-amino-2-phenylquinazolines was parallel to the quinazoline ring and improved their DNA intercalation ability in the DNA-topo I complex. Among the synthesized 4-amino group-substituted analogs, 4-cyclohexylamino-2-phenylquinazoline 7h exhibited potent topo I inhibitory activity and strong cytotoxicity. Interestingly, consistency was observed between the cytotoxicities and topo I activities in these quinazoline analogs, suggesting that the target of 4-amino-2-phenylquinazolines is limited to topo I. Molecular docking studies were performed with the Surflex-Dock program to afford the ideal interaction mode of the compound into the binding site of the DNA-topo I complex in order to clarify the topo I activity of 7h. (C) 2011 Elsevier Ltd. All rights reserved.
• An efficient route towards quinazolinone derivatives via I2-DMSO promoted oxidative decarboxylation of α-amino acid and subsequent oxidative annulation reaction
  作者：Surya Kanta Samanta、Mrinal K. Bera

  DOI：10.1055/a-2065-3169

  日期：——

  An efficient and straightforward strategy to synthesize a wide range of quinazolinone derivatives from commercially inexpensive 2-aminobenzamides and various amino acids via molecular iodine promoted oxidative decarboxylation of α-amino acids, followed by oxidative cyclization reaction, is revealed. Operational simplicity, consistent yield, functional group tolerance and sustainability are the other

  揭示了一种有效且直接的策略，通过分子碘从商业廉价的 2-氨基苯甲酰胺和各种氨基酸合成各种喹唑啉酮衍生物，促进 α-氨基酸的氧化脱羧，然后进行氧化环化反应。操作简单、产量一致、官能团耐受性和可持续性是该反应的其他值得注意的特征。采用目前的策略可以方便地制备大量喹唑啉酮衍生物。在相同的反应条件下合成其他相关的杂芳烃，如苯并恶唑和苯并噻唑衍生物，拓宽了该方法的范围。