<(3-oxo-1,2,4-triazol-5-yl)thio>acetic acid | 141956-66-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: <(3-oxo-1,2,4-triazol-5-yl)thio>acetic acid
• 英文别名: 2-[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)sulfanyl]acetic acid；2-[(5-oxo-1,4-dihydro-1,2,4-triazol-3-yl)sulfanyl]acetic acid
• CAS: 141956-66-3
• 化学式: C₄H₅N₃O₃S
• mdl: MFCD18872689
• 分子量: 175.168
• InChiKey: WKSRSZMSLRQZSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<(2-amino-2-phenylethyl)amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamate 、 <(3-oxo-1,2,4-triazol-5-yl)thio>acetic acid 在 五氟苯酚 、 N,N'-二环己基碳二亚胺 作用下， 生成 -<2-<<2-<<<(4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)thio>acetyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamic acid tricyclo<3.3.1.1^3,7>dec-2-yl ester
  参考文献：
  名称：

  Rationally designed "dipeptoid" analogs of CCK. Acid mimics of the potent and selective non-peptide CCK-B receptor antagonist (CI-988)

  摘要：

  This paper outlines the synthesis of selected acid mimics of the non-peptide CCK-B selective antagonist CI-988, 1. CCK-B and CCK-A binding affinities of these analogues are described and their CCK-B affinity and selectivity rationalized by consideration of the pK(a) values, charge distribution, and geometry of the respective acid mimics. Several of the compounds have CCK-B binding affinities similar to the parent carboxylic acid 1 (CCK-B, IC50 = 1.7 nM; pK(a) = 5.6) and span a pK(a) range of <1 (sulfonic acid 27) to >9.5 (5-thio-1,2,4-triazole 24). Among the more active compounds synthesized are tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[2-[[2-[[(3-hydroxy-5-isoxazolyl)acetyl]-amino]-2-phenylethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate (15), tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-[(1-oxo-3-sulfopropyl)amino]-2-phenylethyl]amino]-ethyl]carbamate, monosodium salt (27), and tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-1[(1H-1,2,4-triazol-5-ylsulfinyl)acetyl]amino]-2-phenylethyl]amino]ethyl]carbamic acid (34) which have CCK-B binding affinities of IC50 = 2.6,1.3, and 1.7 nM, CCK-A/-B ratios of 650,780, and 550 and pK(a) values of 6.5, <1, and 7.0, respectively.

  DOI：

  10.1021/jm00092a007
• 作为产物：
  描述：

  (5-Oxo-4,5-dihydro-1H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以100%的产率得到<(3-oxo-1,2,4-triazol-5-yl)thio>acetic acid
  参考文献：
  名称：

  Rationally designed "dipeptoid" analogs of CCK. Acid mimics of the potent and selective non-peptide CCK-B receptor antagonist (CI-988)

  摘要：

  This paper outlines the synthesis of selected acid mimics of the non-peptide CCK-B selective antagonist CI-988, 1. CCK-B and CCK-A binding affinities of these analogues are described and their CCK-B affinity and selectivity rationalized by consideration of the pK(a) values, charge distribution, and geometry of the respective acid mimics. Several of the compounds have CCK-B binding affinities similar to the parent carboxylic acid 1 (CCK-B, IC50 = 1.7 nM; pK(a) = 5.6) and span a pK(a) range of <1 (sulfonic acid 27) to >9.5 (5-thio-1,2,4-triazole 24). Among the more active compounds synthesized are tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[2-[[2-[[(3-hydroxy-5-isoxazolyl)acetyl]-amino]-2-phenylethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate (15), tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-[(1-oxo-3-sulfopropyl)amino]-2-phenylethyl]amino]-ethyl]carbamate, monosodium salt (27), and tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-1[(1H-1,2,4-triazol-5-ylsulfinyl)acetyl]amino]-2-phenylethyl]amino]ethyl]carbamic acid (34) which have CCK-B binding affinities of IC50 = 2.6,1.3, and 1.7 nM, CCK-A/-B ratios of 650,780, and 550 and pK(a) values of 6.5, <1, and 7.0, respectively.

  DOI：

  10.1021/jm00092a007

文献信息

• Rationally designed "dipeptoid" analogs of CCK. Acid mimics of the potent and selective non-peptide CCK-B receptor antagonist (CI-988)
  作者：Martin J. Drysdale、Martyn C. Pritchard、David C. Horwell

  DOI：10.1021/jm00092a007

  日期：1992.7

  This paper outlines the synthesis of selected acid mimics of the non-peptide CCK-B selective antagonist CI-988, 1. CCK-B and CCK-A binding affinities of these analogues are described and their CCK-B affinity and selectivity rationalized by consideration of the pK(a) values, charge distribution, and geometry of the respective acid mimics. Several of the compounds have CCK-B binding affinities similar to the parent carboxylic acid 1 (CCK-B, IC50 = 1.7 nM; pK(a) = 5.6) and span a pK(a) range of <1 (sulfonic acid 27) to >9.5 (5-thio-1,2,4-triazole 24). Among the more active compounds synthesized are tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[2-[[2-[[(3-hydroxy-5-isoxazolyl)acetyl]-amino]-2-phenylethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate (15), tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-[(1-oxo-3-sulfopropyl)amino]-2-phenylethyl]amino]-ethyl]carbamate, monosodium salt (27), and tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-1[(1H-1,2,4-triazol-5-ylsulfinyl)acetyl]amino]-2-phenylethyl]amino]ethyl]carbamic acid (34) which have CCK-B binding affinities of IC50 = 2.6,1.3, and 1.7 nM, CCK-A/-B ratios of 650,780, and 550 and pK(a) values of 6.5, <1, and 7.0, respectively.