N-<(trifluoromethyl)sulfonyl>-β-alanine | 141956-37-8

• 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: N-<(trifluoromethyl)sulfonyl>-β-alanine
• 英文别名: 3-Trifluoromethanesulfonamidopropanoic acid；3-(trifluoromethylsulfonylamino)propanoic acid
• CAS: 141956-37-8
• 化学式: C₄H₆F₃NO₄S
• mdl: MFCD11649572
• 分子量: 221.157
• InChiKey: VVKOBHARLVYDML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  8

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 、 N-<(trifluoromethyl)sulfonyl>-β-alanine 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 -<1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-<<2-<<1-oxo-3-<<(trifluoromethyl)sulfonyl>amino>propyl>amino>-2-phenylethyl>amino>ethyl>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
• 作为试剂：
  描述：

  在 N-溴酞亚胺 、 2,3,5,6-四氟苯甲酸 、 palladium diacetate 、 N-<(trifluoromethyl)sulfonyl>-β-alanine 作用下， 反应 24.0h， 以98%的产率得到
  参考文献：
  名称：

  Pd(II)催化苯胺和苯甲酸衍生物的间C-H溴化和氯化反应

  摘要：

  由于其富电子特性，经典的亲电溴化导致苯胺的邻位和对位溴化。在此，我们报告了使用市售的N-溴邻苯二甲酰亚胺 (NBP) 开发出前所未有的 Pd 催化苯胺衍生物间位 C-H 溴化，克服了苯胺亲电溴化的竞争性邻位/对位选择性。酸添加剂的添加对于该反应的成功至关重要。该反应可以耐受具有各种取代模式的多种底物。此外，具有复杂取代模式的苯甲酸衍生物也可以通过这种温和的溴化反应进行，并且在类似的反应条件下，间-C-H氯化反应也是可行的。直接基团去除的容易性和随后溴化产物的多样化转化证明了该方法的应用潜力，并为药物发现带来了新的机会。

  DOI：

  10.1039/d2sc01834a

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.