methyl (2S)-2-[[4-[(5-bromofuran-2-yl)methoxymethyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate | 228552-46-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[[4-[(5-bromofuran-2-yl)methoxymethyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate
• CAS: 228552-46-3
• 化学式: C₂₆H₂₈BrNO₅S
• 分子量: 546.482
• InChiKey: GPHWYYSELXGMGI-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[4-[(5-bromofuran-2-yl)methoxymethyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Lithium; (S)-2-({5-[5-(4-formyl-phenyl)-furan-2-ylmethoxymethyl]-2'-methyl-biphenyl-2-carbonyl}-amino)-4-methylsulfanyl-butyrate
  参考文献：
  名称：

  Potent and orally bioavailable noncysteine-containing inhibitors of protein farnesyltransferase

  摘要：

  Potent and orally bioavailable nonthiol-containing inhibitors of protein farnesyltransferase are described. Oral bioavailability was achieved by replacement of the pyridyl ether moiety of 1 with a 2-substituted furan ether to give 4. Potency was regained with 2,5-disubstituted furan ethers while maintaining the bioavailability inherent in 4. p-Chlorophenylfuran ether 24 is 0.7 nM in vitro (FTase) and is 32% bioavailable in the mouse, 30% bioavailable in rats, and 21% bioavailable in dogs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00144-4
• 作为产物：
  描述：

  5-溴-2-糠酸 在 N-甲基吗啉 、 lithium hydroxide 、 sodium tetrahydroborate 、 15-冠醚-5 、 TEA 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-2-[[4-[(5-bromofuran-2-yl)methoxymethyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Potent and orally bioavailable noncysteine-containing inhibitors of protein farnesyltransferase

  摘要：

  Potent and orally bioavailable nonthiol-containing inhibitors of protein farnesyltransferase are described. Oral bioavailability was achieved by replacement of the pyridyl ether moiety of 1 with a 2-substituted furan ether to give 4. Potency was regained with 2,5-disubstituted furan ethers while maintaining the bioavailability inherent in 4. p-Chlorophenylfuran ether 24 is 0.7 nM in vitro (FTase) and is 32% bioavailable in the mouse, 30% bioavailable in rats, and 21% bioavailable in dogs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00144-4

文献信息

• Potent and orally bioavailable noncysteine-containing inhibitors of protein farnesyltransferase
  作者：David J. Augeri、Dave Janowick、Douglas Kalvin、Gerry Sullivan、John Larsen、Daniel Dickman、Hong Ding、Jerry Cohen、Jang Lee、Robert Warner、Peter Kovar、Sajeev Cherian、Badr Saeed、Haichao Zhang、Steve Tahir、Shi-Chung Ng、Hing Sham、Saul H. Rosenberg

  DOI：10.1016/s0960-894x(99)00144-4

  日期：1999.4

  Potent and orally bioavailable nonthiol-containing inhibitors of protein farnesyltransferase are described. Oral bioavailability was achieved by replacement of the pyridyl ether moiety of 1 with a 2-substituted furan ether to give 4. Potency was regained with 2,5-disubstituted furan ethers while maintaining the bioavailability inherent in 4. p-Chlorophenylfuran ether 24 is 0.7 nM in vitro (FTase) and is 32% bioavailable in the mouse, 30% bioavailable in rats, and 21% bioavailable in dogs. (C) 1999 Elsevier Science Ltd. All rights reserved.