N,N'-bis-(4-chloro-benzenesulfonyl)-sulfur diimide | 851-07-0

• 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: N,N'-bis-(4-chloro-benzenesulfonyl)-sulfur diimide
• 英文别名: 4-chloro-N-[(4-chlorophenyl)sulfonylimino-lambda4-sulfanylidene]benzenesulfonamide；4-chloro-N-[(4-chlorophenyl)sulfonylimino-λ4-sulfanylidene]benzenesulfonamide
• CAS: 851-07-0
• 化学式: C₁₂H₈Cl₂N₂O₄S₃
• 分子量: 411.311
• InChiKey: MQZXXCKUKYDRDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  549.2±60.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N'-bis-(4-chloro-benzenesulfonyl)-sulfur diimide 在 三氯化铝 、 Proton Sponge 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 N-methyl-N-(p-chlorophenylsulfonyl)-S-aminosulfeniminopenicillanic acid
  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：

  N,N-dichloro-4-chlorobenzenesulfonamide 在 碘 、 sulfur 作用下， 以 四氯化碳 为溶剂， 生成 N,N'-bis-(4-chloro-benzenesulfonyl)-sulfur diimide
  参考文献：
  名称：

  Markovskii,L.N. et al., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 2522 - 2526

  摘要：

  DOI：

文献信息

• Pel'kis, N. P.; Levchenko, E. S., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1963 - 1967
  作者：Pel'kis, N. P.、Levchenko, E. S.

  DOI：——

  日期：——
• Levchenko, E. S.; Pel'kis, N. P., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 2, p. 398
  作者：Levchenko, E. S.、Pel'kis, N. P.

  DOI：——

  日期：——
• Fischer, E.; Rembarz, G.; Teller, M., Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 6, p. 920 - 924
  作者：Fischer, E.、Rembarz, G.、Teller, M.

  DOI：——

  日期：——
• Shermolovich,Yu.G. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 664 - 667
  作者：Shermolovich,Yu.G. et al.

  DOI：——

  日期：——
• Reaktionen mit N-sulfinylverbindungen, V.: Bis-N-sulfonylsulfodiimide
  作者：W. Wucherpfenning、G. Kreße

  DOI：10.1016/s0040-4039(01)99775-8

  日期：1966.1