(3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-chlorophenyl)methyl>-2-oxetanone | 157457-77-7

• 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: (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-chlorophenyl)methyl>-2-oxetanone
• 英文别名: (3S,4R)-4-[(4-chlorophenyl)methyl]-3-[(2-nitrophenyl)sulfanylamino]oxetan-2-one
• CAS: 157457-77-7
• 化学式: C₁₆H₁₃ClN₂O₄S
• 分子量: 364.809
• InChiKey: PNKRULLAQDFDHY-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸 、 (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-chlorophenyl)methyl>-2-oxetanone 在 4-甲苯硫酚 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(3S,4R)-3-Amino-4-<(4-chlorophenyl)methyl>-2-oxetanone 4-toluenesulfonate
  参考文献：
  名称：

  Synthesis, Stability, and Antimicrobial Activity of (+)-Obafluorin and Related .beta.-Lactone Antibiotics

  摘要：

  Optically pure obafluorin(l), an antibacterial agent from Pseudomonas fluorescens, was synthesized in six steps via lactonization of N-[(2-nitrophenyl)sulfenyl]-(2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid (12a), which was prepared in a stereospecific manner from 4-nitrophenylacetaldehyde (9a) and (S)-1-benzoyl-2-tert-butyl-3-methyl-4-imidazolidinone (7). A series of analogues was then synthesized in order to probe structural features required for antibacterial activity as well as those responsible for the hydrolytic decomposition of 1 to the corresponding hydroxy acid 23a. Analogues 22b and 22e wherein the nitro group of 1 is replaced with hydrogen and chlorine, respectively, were prepared in a fashion similar to 1, as were the N-acetyl, N-benzoyl, and N-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl (ATMO) derivatives 24a-c. The tosylate salt of L-threonine-beta-lactone (21) was transformed to a series of N-acylated derivatives including the following: 22d (2,3-dihydroxybenzoyl), 25 (2-hydroxybenzoyl), 27 (3,4-dihydroxybenzoyl), 29 (4'methyl-2,2'-bipyridine-4-carbonyl), 31 (epsilon-(L-alpha-aminoadipoyl)), 34 ((N'-2,3-dihydroxybenzoyl)-beta-alanyl), 35 (bromoacetyl), 36 ((6-purinylthio)acetyl), and 37 ((4-pyridylthio)acetyl). The results show that a-amino beta-lactones bearing an N-acyl group with an o- or p-hydroxybenzoyl moiety are especially prone to decomposition under aqueous conditions and that this effect is enhanced by replacement of the 4-nitrobenzyl group on the oxetanone ring of 1 with a methyl. The N-(3,4-dihydroxybenzoyl)L-threonine beta-lactone (27) converts slowly in the solid state to (4S,5S)-2-(3,4-dihydroxybenzoyl)-5-methyl-2-oxazoline-4-carboxylic acid (39b), which hydrolyzes rapidly in 4:1 CD3CN:D2O to O-(3,4-dihydroxybenzoyl)-L-allothreonine (38b). Direct hydrolysis of 27 to 38b under the same conditions has a half-life of 2.4 days. Preliminary assays for antibacterial activity indicate that 29 has nearly comparable activity to obafluorin(l) but is much more stable. The (2-nitrophenyl)sulfenyl p-lactones 14 and 41, as well as the N-(phenylsulfenyl)-L-threonine beta-lactone (44), are the most active agents in the biological assays.

  DOI：

  10.1021/jo00092a025
• 作为产物：
  描述：

  (4-氯苯基)乙醛 在 吡啶 、 sodium hydroxide 、 4-溴苯磺酰氯 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.33h， 生成 (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-chlorophenyl)methyl>-2-oxetanone
  参考文献：
  名称：

  Synthesis, Stability, and Antimicrobial Activity of (+)-Obafluorin and Related .beta.-Lactone Antibiotics

  摘要：

  Optically pure obafluorin(l), an antibacterial agent from Pseudomonas fluorescens, was synthesized in six steps via lactonization of N-[(2-nitrophenyl)sulfenyl]-(2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid (12a), which was prepared in a stereospecific manner from 4-nitrophenylacetaldehyde (9a) and (S)-1-benzoyl-2-tert-butyl-3-methyl-4-imidazolidinone (7). A series of analogues was then synthesized in order to probe structural features required for antibacterial activity as well as those responsible for the hydrolytic decomposition of 1 to the corresponding hydroxy acid 23a. Analogues 22b and 22e wherein the nitro group of 1 is replaced with hydrogen and chlorine, respectively, were prepared in a fashion similar to 1, as were the N-acetyl, N-benzoyl, and N-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl (ATMO) derivatives 24a-c. The tosylate salt of L-threonine-beta-lactone (21) was transformed to a series of N-acylated derivatives including the following: 22d (2,3-dihydroxybenzoyl), 25 (2-hydroxybenzoyl), 27 (3,4-dihydroxybenzoyl), 29 (4'methyl-2,2'-bipyridine-4-carbonyl), 31 (epsilon-(L-alpha-aminoadipoyl)), 34 ((N'-2,3-dihydroxybenzoyl)-beta-alanyl), 35 (bromoacetyl), 36 ((6-purinylthio)acetyl), and 37 ((4-pyridylthio)acetyl). The results show that a-amino beta-lactones bearing an N-acyl group with an o- or p-hydroxybenzoyl moiety are especially prone to decomposition under aqueous conditions and that this effect is enhanced by replacement of the 4-nitrobenzyl group on the oxetanone ring of 1 with a methyl. The N-(3,4-dihydroxybenzoyl)L-threonine beta-lactone (27) converts slowly in the solid state to (4S,5S)-2-(3,4-dihydroxybenzoyl)-5-methyl-2-oxazoline-4-carboxylic acid (39b), which hydrolyzes rapidly in 4:1 CD3CN:D2O to O-(3,4-dihydroxybenzoyl)-L-allothreonine (38b). Direct hydrolysis of 27 to 38b under the same conditions has a half-life of 2.4 days. Preliminary assays for antibacterial activity indicate that 29 has nearly comparable activity to obafluorin(l) but is much more stable. The (2-nitrophenyl)sulfenyl p-lactones 14 and 41, as well as the N-(phenylsulfenyl)-L-threonine beta-lactone (44), are the most active agents in the biological assays.

  DOI：

  10.1021/jo00092a025

文献信息

• Synthesis, Stability, and Antimicrobial Activity of (+)-Obafluorin and Related .beta.-Lactone Antibiotics
  作者：Yunlong Pu、Christopher Lowe、Miloslav Sailer、John C. Vederas

  DOI：10.1021/jo00092a025

  日期：1994.7

  Optically pure obafluorin(l), an antibacterial agent from Pseudomonas fluorescens, was synthesized in six steps via lactonization of N-[(2-nitrophenyl)sulfenyl]-(2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid (12a), which was prepared in a stereospecific manner from 4-nitrophenylacetaldehyde (9a) and (S)-1-benzoyl-2-tert-butyl-3-methyl-4-imidazolidinone (7). A series of analogues was then synthesized in order to probe structural features required for antibacterial activity as well as those responsible for the hydrolytic decomposition of 1 to the corresponding hydroxy acid 23a. Analogues 22b and 22e wherein the nitro group of 1 is replaced with hydrogen and chlorine, respectively, were prepared in a fashion similar to 1, as were the N-acetyl, N-benzoyl, and N-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl (ATMO) derivatives 24a-c. The tosylate salt of L-threonine-beta-lactone (21) was transformed to a series of N-acylated derivatives including the following: 22d (2,3-dihydroxybenzoyl), 25 (2-hydroxybenzoyl), 27 (3,4-dihydroxybenzoyl), 29 (4'methyl-2,2'-bipyridine-4-carbonyl), 31 (epsilon-(L-alpha-aminoadipoyl)), 34 ((N'-2,3-dihydroxybenzoyl)-beta-alanyl), 35 (bromoacetyl), 36 ((6-purinylthio)acetyl), and 37 ((4-pyridylthio)acetyl). The results show that a-amino beta-lactones bearing an N-acyl group with an o- or p-hydroxybenzoyl moiety are especially prone to decomposition under aqueous conditions and that this effect is enhanced by replacement of the 4-nitrobenzyl group on the oxetanone ring of 1 with a methyl. The N-(3,4-dihydroxybenzoyl)L-threonine beta-lactone (27) converts slowly in the solid state to (4S,5S)-2-(3,4-dihydroxybenzoyl)-5-methyl-2-oxazoline-4-carboxylic acid (39b), which hydrolyzes rapidly in 4:1 CD3CN:D2O to O-(3,4-dihydroxybenzoyl)-L-allothreonine (38b). Direct hydrolysis of 27 to 38b under the same conditions has a half-life of 2.4 days. Preliminary assays for antibacterial activity indicate that 29 has nearly comparable activity to obafluorin(l) but is much more stable. The (2-nitrophenyl)sulfenyl p-lactones 14 and 41, as well as the N-(phenylsulfenyl)-L-threonine beta-lactone (44), are the most active agents in the biological assays.