2-(1-Bromoethyl)-3-benzyl-quinazolin-4-one | 770743-61-8

• 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-(1-Bromoethyl)-3-benzyl-quinazolin-4-one
• 英文别名: 3-benzyl-2-(1-bromoethyl)quinazolin-4-one
• CAS: 770743-61-8
• 化学式: C₁₇H₁₅BrN₂O
• 分子量: 343.223
• InChiKey: KBEMQNSEDAIXOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-Bromoethyl)-3-benzyl-quinazolin-4-one 在 sodium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[1-(3-Benzyl-4-oxoquinazolin-2-yl)ethyl]-3-(3-chlorophenyl)-1-(2,4-dimethoxyphenyl)urea
  参考文献：
  名称：

  Quinazolinone-based fungal efflux pump inhibitors. Part 1: Discovery of an (N-methylpiperazine)-containing derivative with activity in clinically relevant Candida spp.

  摘要：

  The discovery of a series of quinazolinone-based fungal efflux pump inhibitors by high-throughput screening for potentiation of fluconazole in C. albicans is described. Attempts to improve the aqueous solubility of screening hits led to the discovery of an analog with greatly improved physical properties and activity against clinically-relevant Candida spp. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.070
• 作为产物：
  描述：

  2-乙基-苯并[d][1,3]噁嗪-4-酮 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 生成 2-(1-Bromoethyl)-3-benzyl-quinazolin-4-one
  参考文献：
  名称：

  Quinazolinone-based fungal efflux pump inhibitors. Part 1: Discovery of an (N-methylpiperazine)-containing derivative with activity in clinically relevant Candida spp.

  摘要：

  The discovery of a series of quinazolinone-based fungal efflux pump inhibitors by high-throughput screening for potentiation of fluconazole in C. albicans is described. Attempts to improve the aqueous solubility of screening hits led to the discovery of an analog with greatly improved physical properties and activity against clinically-relevant Candida spp. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.070
• 作为试剂：
  描述：

  、 N-(1-benzoylethyl)-2-(formylamino)-benzamide 、 溴 、 溶剂黄146 在 2-(1-Bromoethyl)-3-benzyl-quinazolin-4-one 作用下， 以to provide 2-(1-bromoethyl)-3-benzyl-quinazolin-4-one (“Compound F”)的产率得到2-(1-Bromoethyl)-3-benzyl-quinazolin-4-one
  参考文献：
  名称：

  Modulators of Rho C activity

  摘要：

  式子1的化合物可以调节Rho C的活性：其中R1为H、低碳基、芳基-烷基、芳基-低烯基或—(CH2)nCH(R7)NR8R9，其中n为0至6之间，R7为H、低碳基、芳基或芳基-烷基，R8为H、低碳基、环烷基、芳基或芳基-烷基，R9为R、RCO—、ROCO—或RNHCO—，其中R为低碳基、环烷基、芳基或芳基-烷基，其中芳基和芳基-烷基被0至3个取自低碳基、卤素、硝基、—OH、三氟甲基或低烷氧基的取代基所取代；R2为低碳基、芳基、芳基-烷基或—(CHR10)m—(CO)—R11，其中m为0至4，R10为H或低碳基，R11为低碳基、环烷基、芳基或芳基-烷基，其中芳基和芳基-烷基被0至3个取自低碳基、卤素、硝基、—OH、三氟甲基或低烷氧基的取代基所取代；R3、R4、R5和R6各自独立地为H、低碳基、卤素、硝基、—OH、低烷氧基、NH2、低碳基氨基、二(低碳基)氨基、三氟甲基或SH；或其药学上可接受的盐。

  公开号：

  US07053216B2

文献信息

• US7053216B2
  申请人：——

  公开号：US7053216B2

  公开（公告）日：2006-05-30
• [EN] MODULATORS OF RHO C ACTIVITY<br/>[FR] MODULATEURS DE L'ACTIVITE DE RHO C
  申请人：ICONIX PHARM INC

  公开号：WO2003043961A2

  公开（公告）日：2003-05-30

  Compounds of formula 1 modulate the activity of Rho C: (Formula I) wherein R1 is H, lower alkyl, aralkyl, aryl-lower alkenyl, or (CH2)nCH(R7)NR8R9, where n is 0-6 inclusive, R7 is H, lower alkyl, aryl, or aralkyl, R8 is H, lower alkyl, cyclo-alkyl, aryl, or aralkyl, and R9 is R, RCO-, ROCO-, or RNHCO-, where R is lower alkyl, cycloalkyl, aryl, or aralkyl, wherein aryl and aralkyl are substituted with 0-3 substituents selected from the group consisting of lower alkyl, halo, nitro, -OH, trifluoromethyl, or lower alkoxy; R2 is lower alkyl, aryl, aralkyl, or (CHR10)m-(CO)-R11, wherein m is 0-4, R10 is H or lower alkyl, and R11 is lower alkyl, cycloalkyl, aryl, or aralkyl, wherein aryl and aralkyl are substituted with 0-3 substituents selected from the group consisting of lower alkyl, halo, nitro, -OH, trifluoromethyl, or lower alkoxy; R3, R4, R5 and R6 are each independtly H, lower alkyl, halo, nitro, OH, lowe alkoxy, NH2, lower alkylamino, di(lower alkylamino), trifluoromethyl, or SH; or a pharmaceutically acceptable salt thereof.
• Quinazolinone-based fungal efflux pump inhibitors. Part 1: Discovery of an (N-methylpiperazine)-containing derivative with activity in clinically relevant Candida spp.
  作者：Rémy C. Lemoine、Tomasz W. Glinka、William J. Watkins、Aesop Cho、Jessie Yang、Nadeem Iqbal、Rajeshwar Singh、Deidre Madsen、Karen Lolans、Olga Lomovskaya、Uma Oza、Michael N. Dudley

  DOI：10.1016/j.bmcl.2004.07.070

  日期：2004.10

  The discovery of a series of quinazolinone-based fungal efflux pump inhibitors by high-throughput screening for potentiation of fluconazole in C. albicans is described. Attempts to improve the aqueous solubility of screening hits led to the discovery of an analog with greatly improved physical properties and activity against clinically-relevant Candida spp. (C) 2004 Elsevier Ltd. All rights reserved.
• Modulators of Rho C activity
  申请人：——

  公开号：US20030171387A1

  公开（公告）日：2003-09-11

  Compounds of formula 1 modulate the activity of Rho C: 1 wherein R 1 is H, lower alkyl, aralkyl, aryl-lower alkenyl, or —(CH 2 ) n CH(R 7 )NR 8 R 9 , where n is 0-6 inclusive, R 7 is H, lower alkyl, aryl, or aralkyl, R 8 is H, lower alkyl, cyclo-alkyl, aryl, or aralkyl, and R 9 is R, RCO—, ROCO—, or RNHCO—, where R is lower alkyl, cycloalkyl, aryl, or aralkyl, wherein aryl and aralkyl are substituted with 0-3 substituents selected from the group consisting of lower alkyl, halo, nitro, —OH, trifluoromethyl, or lower alkoxy; R 2 is lower alkyl, aryl, aralkyl, or —(CHR 10 ) m (CO)—R 11 , wherein m is 0-4, R 10 is H or lower alkyl, and R 11 is lower alkyl, cycloalkyl, aryl, or aralkyl, wherein aryl and aralkyl are substituted with 0-3 substituents selected from the group consisting of lower alkyl, halo, nitro, —OH, trifluoromethyl, or lower alkoxy; R 3 , R 4 , R 5 , and R 6 , are each independently H, lower alkyl, halo, nitro, OH, lower alkoxy, NH 2 , lower alkylamino, di(lower alkylamino), trifluoromethyl, or SH; or a pharmaceutically acceptable salt thereof.

  式子1的化合物调节Rho C的活性，其中R1为氢、低烷基、芳基烷基、芳基-低烯基或—(CH2)nCH(R7)NR8R9，其中n为0-6，R7为氢、低烷基、芳基或芳基烷基，R8为氢、低烷基、环烷基、芳基或芳基烷基，R9为R、RCO—、ROCO—或RNHCO—，其中R为低烷基、环烷基、芳基或芳基烷基，其中芳基和芳基烷基被0-3个来自下列基团的取代基取代：低烷基、卤素、硝基、—OH、三氟甲基或低烷氧基；R2为低烷基、芳基、芳基烷基或—(CHR10)m(CO)—R11，其中m为0-4，R10为氢或低烷基，R11为低烷基、环烷基、芳基或芳基烷基，其中芳基和芳基烷基被0-3个来自下列基团的取代基取代：低烷基、卤素、硝基、—OH、三氟甲基或低烷氧基；R3、R4、R5和R6各自独立地为氢、低烷基、卤素、硝基、—OH、低烷氧基、NH2、低烷基氨基、二(低烷基)氨基、三氟甲基或SH；或其药学上可接受的盐。