1-methyl-1-<(4-methoxyphenyl)sulfonyl>hydrazine | 98394-35-5

• 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: 1-methyl-1-<(4-methoxyphenyl)sulfonyl>hydrazine
• 英文别名: 1-<(4-methylphenyl)sulfonyl>-1-methylhydrazine；4-methoxy-N-methylbenzenesulfonohydrazide
• CAS: 98394-35-5
• 化学式: C₈H₁₂N₂O₃S
• 分子量: 216.261
• InChiKey: GYEMUZKGVFHSFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 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：
  81
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-1-<(4-methoxyphenyl)sulfonyl>hydrazine 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 1-乙酸基-1,2-苯碘酰-3-(1H)-酮 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 N-(1-(4-fluorophenyl)-1H-indol-2-yl)-4-methoxy-N-methylbenzenesulfonamide
  参考文献：
  名称：

  高价碘试剂可实现（杂）芳烃与亚氨基苯乙酸的 C(sp2)–H 酰胺化

  摘要：

  含磺酰胺的（杂）芳烃广泛存在于生物活性分子中。在这里，我们报告了通过 C(sp 2 )-H 酰胺化从台式稳定的酰胺基-亚氨基苯乙酸合成磺胺基（杂）芳烃。高价碘试剂共价活化亚氨基苯乙酸，在温和的光催化氧化条件下容易产生磺胺自由基。多样化的吲哚、吡咯、咪唑并吡啶和稠合芳烃经过 C(sp 2 )-H 酰胺化，具有优异的化学选择性和区域选择性。该反应在具有潜在生物学应用的中性水性条件下表现良好。

  DOI：

  10.1021/acs.orglett.2c02751
• 作为产物：
  描述：

  甲基肼 、 对甲氧基苯磺酰氯 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到1-methyl-1-<(4-methoxyphenyl)sulfonyl>hydrazine
  参考文献：
  名称：

  Synthesis and evaluation of 1-(arylsulfonyl)-2-[(methoxycarbonyl)sulfenyl]-1-methylhydrazines as antineoplastic agents

  摘要：

  1-(Arylsulfonyl)-2-[(methoxycarbonyl)sulfenyl]-1-methylhydrazines, with the potential to function as biological methylating agents, were synthesized and evaluated as antineoplastic agents against the L1210 leukemia and the B16 melanoma in mice. All of the compounds of this class had significant activity against the B16 melanoma, with the most active compound, 2-[(methoxycarbonyl)sulfenyl]-1-methyl-1-[(4- methylphenyl)sulfonyl]hydrazine, producing percent T/C values for B16 melanoma tumor bearing mice of between 182 and 232 at dosage levels of from 12.5 to 50 mg/kg daily for 6 consecutive days. In contrast to the related class of agents, the N,N'-bis(sulfonyl)hydrazines reported earlier by this laboratory,1 the 1-(arylsulfonyl)-2-[(methoxycarbonyl)sulfenyl]-1-methylhydrazines were found to be inactive against the L1210 leukemia in vivo.

  DOI：

  10.1021/jm00159a036

文献信息

• 1,2-Bis(sulfonyl)hydrazines. 3. Effects of structural modification on antineoplastic activity
  作者：Krishnamurthy Shyam、Robert T. Hrubiec、Ryosuke Furubayashi、Lucille A. Cosby、Alan C. Sartorelli

  DOI：10.1021/jm00394a040

  日期：1987.11

  A series of 1,2-bis(sulfonyl)hydrazines was synthesized and evaluated for antineoplastic activity against the L1210 leukemia and the B16 melanoma. The most active agent to emerge from this study, 1,2-bis(methylsulfonyl)-1-methylhydrazine, produced a maximum % T/C for mice bearing the L1210 leukemia or the B16 melanoma of 340% and 278%, respectively. Two N-chloroethyl analogues, conceived as bifunctional alkylating agents, were also synthesized and evaluated for antineoplastic activity against the L1210 leukemia and the B16 melanoma. Although such a modification resulted in retention of antineoplastic activity against both tumor cell lines, it did not result in enhanced antineoplastic activity.
• 1,2-Bis(arylsulfonyl)hydrazines. 2. The influence of arenesulfonyl and aralkylsulfonyl substituents on antitumor and alkylating activity
  作者：Krishnamurthy Shyam、Lucille A. Cosby、Alan C. Sartorelli

  DOI：10.1021/jm00157a041

  日期：1986.7

  Several 1,2-bis(arylsulfonyl)-1-methylhydrazines were synthesized and evaluated for antineoplastic activity against the L1210 leukemia. The most active compound to emerge from this study, 2-[(4-chlorophenyl)sulfonyl]-1-methyl-1-(4-tolylsulfonyl)hydrazine , increased the survival time of tumor-bearing mice by 88%. The alkylating activity of the synthesized analogues and several compounds reported earlier was determined by measuring the absorbance at 540 nm of the alkylated product of 4-(4-nitrobenzyl)pyridine. The results obtained support the concept that the ability to alkylate is a necessary but not a sufficient condition for the expression of antitumor activity by agents of this class.
• SARTORELLI, ALAN C.;SHYAM, KRISHNAMURTHY;HRUBIEC, ROBERT T.
  作者：SARTORELLI, ALAN C.、SHYAM, KRISHNAMURTHY、HRUBIEC, ROBERT T.

  DOI：——

  日期：——
• SHYAM KRISHNAMURTHY; RYOSUKE FURUBAYASHI; HRUBIEC R. T.; COSBY L. A.; SAR+, J. MED. CHEM., 29,(1986) N 7, 1323-1325
  作者：SHYAM KRISHNAMURTHY、 RYOSUKE FURUBAYASHI、 HRUBIEC R. T.、 COSBY L. A.、 SAR+

  DOI：——

  日期：——
• HRUBIEC R. T.; SHYAM KRISHNAMURTHY; COSBY L. A.; SARTORELLI A. C., J. MED. CHEM., 29,(1986) N 9, 1777-1779
  作者：HRUBIEC R. T.、 SHYAM KRISHNAMURTHY、 COSBY L. A.、 SARTORELLI A. C.

  DOI：——

  日期：——