4-chloro-N-sulfinyl-benzenesulfonamide | 52867-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-sulfinyl-benzenesulfonamide
• 英文别名: N-(4-chloro-benzenesulfonyl)-sulfur imide oxide；Benzenesulfonamide, 4-chloro-N-sulfinyl-；4-chloro-N-sulfinylbenzenesulfonamide
• CAS: 52867-26-2
• 化学式: C₆H₄ClNO₃S₂
• 分子量: 237.688
• InChiKey: FSCUIRIFQOSPBO-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  350.1±44.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-N-sulfinyl-benzenesulfonamide 在 吡啶 、 Proton Sponge 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 diphenylmethyl N-methyl-N-(p-chlorophenylsulfonyl)-S-aminosulfeniminopenicillanate
  参考文献：
  名称：

  S-Aminosulfeniminopenicillins:  Multimode β-Lactamase Inhibitors and Template Structures for Penicillin-Based β-Lactamase Substrates as Prodrugs

  摘要：

  A series of novel penicillins, bearing an S-aminosulfenimine (R'(R ")NSN=) side chain at the 6-position, have been prepared by direct reaction of a penicillin eater with sulfur diimides. A set of these structures, with the thiazolidine-ring sulfur in the sulfide oxidation state, exhibited a pattern of reactivity not previously encountered in penicillin chemistry, viz., cleavage of the beta-lactam ring resulted in a rapid intramolecular displacement of the S-amino moiety as R'(R ")NH. This was found to be the exclusive reaction occurring consequent on cleavage of the p-lactam ring. The mechanism of this process was delineated in a detailed study in basic methanol. That a similar reactivity pattern held for a penicillin salt in aqueous solution was also verified. Thus the salt 5bm (R' = CH3, R " = p-CH3C6H4SO2) behaved as a moderate substrate for beta-lactamase type I from Bacillus cereus (k(cat)/K-m = 6.26 x 10(5) M-1 min(-1)). On enzyme-catalyzed hydrolysis of this compound, displacement of N-methyl-p-toluenesulfonamide (R'(R ")NH) was directly observed (H-1 NMR) and found to occur faster than displacement of this group from (intact) 5bm in aqueous buffer, by a factor of at least 600. These findings identified the potential of the S-aminosulfeniminopenicillin structure type to be developed as beta-lactamase substrates for use as site-specific-release prodrugs. A degree of enzyme inhibition was also observed with this set of thiazolidinering-sulfide structures with the most potent inhibitor having the most nucleofugic S-amino moiety p-ClC6H4SO2N(CH3), indicating that displacement of this group, at the enzyme active site, played a role in their mode of inhibition. Structures with the thiazolidine-ring sulfur in the sulfone oxidation state were considerably more potent as inhibitors, with the structure 5a(2) being the most active. As this compound bore the least nucleofugic S-amino moiety C2H5OC(O)NH, it indicated that the mode of inhibition of the sulfones was distinct from that of the thiazolidine-ring sulfides; it is probable that the sulfones reacted in a manner similar to that shown by sulbactam viz., rapid scission of the thiazolidine-sulfone ring after cleavage of the beta-lactam ring. Synergy of action was observed with 5a(2) at high concentration (78 mu g/mL) against Escherichia coli when combined 1:1 with penicillin G; no synergy was observed at low concentration (4 mu g/mL) when combined with pipericillin, indicating poor permeation characteristics.

  DOI：

  10.1021/jo970737f
• 作为产物：
  描述：

  4-氯苯磺酰胺 在 氯化亚砜 作用下， 反应 20.0h， 以96.6%的产率得到4-chloro-N-sulfinyl-benzenesulfonamide
  参考文献：
  名称：

  S-Aminosulfeniminopenicillins:  Multimode β-Lactamase Inhibitors and Template Structures for Penicillin-Based β-Lactamase Substrates as Prodrugs

  摘要：

  A series of novel penicillins, bearing an S-aminosulfenimine (R'(R ")NSN=) side chain at the 6-position, have been prepared by direct reaction of a penicillin eater with sulfur diimides. A set of these structures, with the thiazolidine-ring sulfur in the sulfide oxidation state, exhibited a pattern of reactivity not previously encountered in penicillin chemistry, viz., cleavage of the beta-lactam ring resulted in a rapid intramolecular displacement of the S-amino moiety as R'(R ")NH. This was found to be the exclusive reaction occurring consequent on cleavage of the p-lactam ring. The mechanism of this process was delineated in a detailed study in basic methanol. That a similar reactivity pattern held for a penicillin salt in aqueous solution was also verified. Thus the salt 5bm (R' = CH3, R " = p-CH3C6H4SO2) behaved as a moderate substrate for beta-lactamase type I from Bacillus cereus (k(cat)/K-m = 6.26 x 10(5) M-1 min(-1)). On enzyme-catalyzed hydrolysis of this compound, displacement of N-methyl-p-toluenesulfonamide (R'(R ")NH) was directly observed (H-1 NMR) and found to occur faster than displacement of this group from (intact) 5bm in aqueous buffer, by a factor of at least 600. These findings identified the potential of the S-aminosulfeniminopenicillin structure type to be developed as beta-lactamase substrates for use as site-specific-release prodrugs. A degree of enzyme inhibition was also observed with this set of thiazolidinering-sulfide structures with the most potent inhibitor having the most nucleofugic S-amino moiety p-ClC6H4SO2N(CH3), indicating that displacement of this group, at the enzyme active site, played a role in their mode of inhibition. Structures with the thiazolidine-ring sulfur in the sulfone oxidation state were considerably more potent as inhibitors, with the structure 5a(2) being the most active. As this compound bore the least nucleofugic S-amino moiety C2H5OC(O)NH, it indicated that the mode of inhibition of the sulfones was distinct from that of the thiazolidine-ring sulfides; it is probable that the sulfones reacted in a manner similar to that shown by sulbactam viz., rapid scission of the thiazolidine-sulfone ring after cleavage of the beta-lactam ring. Synergy of action was observed with 5a(2) at high concentration (78 mu g/mL) against Escherichia coli when combined 1:1 with penicillin G; no synergy was observed at low concentration (4 mu g/mL) when combined with pipericillin, indicating poor permeation characteristics.

  DOI：

  10.1021/jo970737f

文献信息

• Das Reaktionsverhalten acylierter Heterokumulene gegenüber Phospholenen. 1. Mitt
  作者：R. Neidlein、R. Mosebach

  DOI：10.1002/ardp.19743070410

  日期：——

  gegenüber Phospholenen berichtet; so entstehen substituierte N‐Sulfonyl‐1,3,2‐oxasulfinazole (5) aus unterschiedlich substituierten Phospholenen sowie 3 Gemische von isomeren N‐Sulfonyl‐1,3,2‐oxasulfinazolen (8, 9). N‐Sulfonyl‐isothiocyanate (12) ergaben mit 11 die N‐Sulfonyl‐Δ 4 – 1,3‐oxazolin‐2‐thione (13). – IR‐ und Massenspektren dienten zur Strukturaufklärung der neuen Verbindungen.

  报道了N-磺酰基-杂枯草烯对磷烯的反应行为；因此，取代的 N-磺酰基-1,3,2-氧杂亚磺腈 (5) 由不同取代的磷烯以及异构 N-磺酰基-1,3,2-氧杂亚磺腈 (8, 9) 的 3 种混合物形成。N-磺酰基-异硫氰酸酯 (12) 得到 N-磺酰基-Δ 4 - 1,3-恶唑啉-2-硫酮 (13) 和 11。- 红外光谱和质谱用于阐明新化合物的结构。
• Darstellung und eigenschaften von 124,2,4,6-thiatriazin-1-oxiden. zur struktur der hydrolyseprodukte von 1-arensulfonyl-imino-1λ4,2,4,6-thiatriazinen
  作者：E. Fischer、M. Teller、A. Kálmán、Gy. Argay

  DOI：10.1016/s0040-4020(01)91186-x

  日期：1984.1

  Synthesis and structure of 4-phenoxy-H[1λ4,2,4,6]thiatriazino[4,3a]benzimidazole-2-oxide 5, 3-amino-4H[1λ4,2,4,6]thiatriazino[2,3-a]benzimidazole-1-oxide 6 and 3-amino-5-dimethylamino-2-tosyl-1λ4, 2,4,6-thiatriazine-1-oxide 7, obtained by hydrolysis of the corresponding arenesulfonyl imino compounds are discussed. The molecular and crystal structure of N-benzoyl-Ń tosyl-guanidine is presented.

  合成和结构4-苯氧基- H [1λ 4，2,4,6] thiatriazino并[4,3a]苯并咪唑-2-氧化物5，3-氨基-4- ħ [1λ 4，2,4,6] thiatriazino [ 2,3-a]苯并咪唑-1-氧化物6和3-氨基-5-二甲基氨基-2-甲苯磺酰基1λ 4，2,4,6- thiatriazine -1-氧化物7，通过相应的芳烃磺酰基亚氨基的化合物的水解而获得的讨论。介绍了N-苯甲酰基-Ń甲苯磺酰基-胍的分子和晶体结构。
• Markovskii,L.N. et al., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 2104 - 2108
  作者：Markovskii,L.N. et al.

  DOI：——

  日期：——
• Senning,A., Acta Chemica Scandinavica (1947), 1967, vol. 21, p. 1293 - 1296
  作者：Senning,A.

  DOI：——

  日期：——
• Kasper, F.; Dathe, S., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 6, p. 1041 - 1044
  作者：Kasper, F.、Dathe, S.

  DOI：——

  日期：——