N-(3-methanesulfonylamino-propyl)methanesulfonamide | 35688-16-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(3-methanesulfonylamino-propyl)methanesulfonamide
• 英文别名: 1,3-propanediammoniumbismethanesulfonate；N,N'-Trimethylen-bis-methansulfonamid；N-[3-(methanesulfonamido)propyl]methanesulfonamide
• CAS: 35688-16-5
• 化学式: C₅H₁₄N₂O₄S₂
• mdl: MFCD03402409
• 分子量: 230.309
• InChiKey: OWCDTFBGAKPXKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3-methanesulfonylamino-propyl)methanesulfonamide 在 甲酸 、 sodium nitrite 作用下， 生成 N,N'-Trimethylen-bis-(N-nitroso-methansulfonamid)
  参考文献：
  名称：

  Synthesis of Potential Anticancer Agents. XXI. Nitrosated Sulfonamides Related to Myleran

  摘要：

  DOI：

  10.1021/jo01073a024
• 作为产物：
  描述：

  甲基磺酰氯 、 1,3-丙二胺 在 potassium carbonate 作用下， 以 苯 为溶剂， 生成 N-(3-methanesulfonylamino-propyl)methanesulfonamide
  参考文献：
  名称：

  Synthesis of Potential Anticancer Agents. XXI. Nitrosated Sulfonamides Related to Myleran

  摘要：

  DOI：

  10.1021/jo01073a024

文献信息

• Krakowiak, Krzysztof; Idowski, Pawel; Kotelko, Barbara, Polish Journal of Chemistry, 1984, vol. 58, # 1-3, p. 251 - 257
  作者：Krakowiak, Krzysztof、Idowski, Pawel、Kotelko, Barbara

  DOI：——

  日期：——
• Quantitative structure–activity relationships studies for prediction of antimicrobial activity of synthesized disulfonamide derivatives
  作者：Saliha Alyar、Neslihan Özbek、Kübra Kuzukıran、Nurcan Karacan

  DOI：10.1007/s00044-010-9304-7

  日期：2011.3

  A new series of disulfonamides were synthesized and assayed as antimicrobial agents against Staphylococcus aureus, Bacillus cereus, and Escherichia coli. The quantitative structure-activity relationship analysis (QSAR) was applied to find out the correlation between experimentally evaluated antimicrobial activities with various parameters of the compounds using stepwise multiple liner regression method. The QSAR analysis revealed that the third-order average connectivity index ((3)chi(A)) was found to have negative correlation. The best QSAR models were further validated by leave-one-out method of cross-validation.
• Repositioning HIV-1 Integrase Inhibitors for Cancer Therapeutics: 1,6-Naphthyridine-7-carboxamide as a Promising Scaffold with Drug-like Properties
  作者：Li-Fan Zeng、Yong Wang、Roza Kazemi、Shili Xu、Zhong-Liang Xu、Tino W. Sanchez、Liu-Meng Yang、Bikash Debnath、Srinivas Odde、Hua Xie、Yong-Tang Zheng、Jian Ding、Nouri Neamati、Ya-Qiu Long

  DOI：10.1021/jm300667v

  日期：2012.11.26

  Among a large number of HIV-1 integrase (IN) inhibitors, the 8-hydroxy-[1,6]naphthyridines (i.e., L-870,810) were one of the promising class of antiretroviral drugs developed by Merck Laboratories. In spite of its remarkable potency and efficacy, unfortunately upon completion of phase I clinical studies, development of L-870,810 was halted. Because of its desirable pharmacological and pharmaceutical properties we were intrigued to design novel analogues of L-870,810 with goals to (1) improve upon limitations of naphthyridine-7-carboxamides as antiviral agents and (2) to reposition their use as innovative cytotoxic agents for cancer therapeutics. Herein, we report on the design and synthesis of a series of 1,6-naphthyridine-7-carboxamides with various substitutions at the 5- and 8-positions. All the new 5-substituted-8-hydroxy-[1,6]naphthyridines were potent IN inhibitors and the 5-substituted-8-amino-[1,6]naphthyridines were significantly cytotoxic. Further optimization of the 5,8-disubstituted-[1,6]naphthyridines with structural variation on 7-carboxamide delivered novel compounds with significant cytotoxicity in a panel of cancer cell lines and effective inhibition against select oncogenic kinases.
• Lead optimization of HMBA to develop potent HEXIM1 inducers
  作者：Bo Zhong、Rati Lama、Wannarasmi Ketchart、Monica M. Montano、Bin Su

  DOI：10.1016/j.bmcl.2014.01.025

  日期：2014.3

  The potency of a series of Hexamethylene bis-acetamide (HMBA) derivatives inducing Hexamethylene bis-acetamide inducible protein 1 (HEXIM1) was determined in LNCaP prostate cancer cells. Several compounds with unsymmetrical structures showed significantly improved activity. Distinct from HMBA, these analogs have increased hydrophobicity and can improve the short half-life of HMBA, which is one of the factors that have limited the application of HMBA in clinics. The unsymmetrical scaffolds of the new analogs provide the basis for further lead optimization of the compounds using combinatorial chemistry strategy. Published by Elsevier Ltd.
• KRAKOWIAK, K.;KOTELKO, B., ACTA POL. PHARM., 1983, 40, N 3, 319-326
  作者：KRAKOWIAK, K.、KOTELKO, B.

  DOI：——

  日期：——