N-(cyanomethyl)-methanesulfonamide | 142254-19-1

• 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-(cyanomethyl)-methanesulfonamide
• 英文别名: N-(cyanomethyl)methanesulfonamide；methanesulfonamidoacetonitrile
• CAS: 142254-19-1
• 化学式: C₃H₆N₂O₂S
• mdl: MFCD01212948
• 分子量: 134.159
• InChiKey: WKFRGUWSNCMHOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  288.4±42.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(cyanomethyl)-methanesulfonamide 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以72%的产率得到(1Z)-N'-hydroxy-2-[(methylsulfonyl)amino]ethanimidamide
  参考文献：
  名称：

  Potent and Selective Nonpeptidic Inhibitors of Procollagen C-Proteinase

  摘要：

  6-Cyclohexyl-N-hydroxy-3-(1,2,4-oxadiazol-5-yl)hexanamides were previously disclosed as inhibitors of procollagen C-proteinase (PCP) culminating in the identification of amide 1. Our objective was to discover a second inhibitor that would have improved affinity for PCP and to optimize properties for transepidermal delivery (TED) to intact skin. Further investigation of this template identified a number of potent PCP inhibitors (IC50 values of 2-6 nM) with improved TED flux. Sulfonamide 56 had excellent PCP enzyme activity when measured with a peptide substrate (K-i 8.7 nM) or with the endogenous substrate procollagen (IC50 3.4 nM) and demonstrates excellent selectivity over MMPs involved in wound healing (> 10 000-fold). In the fibroplasia model, 56 inhibited deposition of insoluble collagen by 76 +/- 2% at 10 mu M and was very effective at penetrating human skin in vitro with a TED flux of 1.5 mu g/cm(2)/h, which compares favorably with values for agents that are known to penetrate skin well in vivo. Based on this profile, 56 (UK-421,045) was selected as a candidate for further preclinical evaluation as a topically applied, dermal anti-scarring agent.

  DOI：

  10.1021/jm061010z
• 作为产物：
  描述：

  甲基磺酰氯 、 氨基乙腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以31%的产率得到N-(cyanomethyl)-methanesulfonamide
  参考文献：
  名称：

  醛类基质上的CSIC反应

  摘要：

  在方便官能化的氰基烷基磺酸盐和衍生自醛的氰基烷基磺酰胺上进行碳负离子介导的磺酸盐（磺酰胺）分子内环化反应（CSIC反应），可以得到新的杂环体系5-烷基-4-氨基-5 H -1,2-恶唑2 ，2-二氧化物和3-烷基-5 H -4-氨基-5-氰基-5 H -2,3-二氢异噻唑1,1-二氧化物的收率很好。

  DOI：

  10.1016/s0040-4020(00)00124-1

文献信息

• 3-ox(adi) azolylpropanohydroxamic acids useful as procollagen C- Proteinase inhibitors
  申请人：——

  公开号：US20020151535A1

  公开（公告）日：2002-10-17

  Compounds of formula (I): 1 wherein the substituents are as defined herein, and their salt, solvates, and prodrugs are procollagen C-proteinase (PCP) inhibitors useful in treating conditions mediated by PCP.

  式（I）的化合物： 其中取代基如本文所定义，并且它们的盐、溶剂合物和前药是用于治疗由PCP介导的疾病的前胶原C蛋白酶（PCP）抑制剂。
• Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines
  作者：Yitong Chen、Qi Zhu、Haiyang Wang、Yongping Yu、Guolin Zhang、wenteng chen

  DOI：10.1055/a-2051-0933

  日期：——

  An efficient synthesis of unsymmetrical 2,6-disubstituted pyrazines was developed via a palladium(II)-catalyzed cascade reaction from aminoacetonitriles and arylboronic acids. This transformation involves a C(sp)–C(sp2) coupling followed by an intramolecular C–N bond formation in good to excellent yields.

  通过钯 (II) 催化的氨基乙腈和芳基硼酸的级联反应，开发了不对称 2,6-二取代吡嗪的有效合成。这种转化涉及 C(sp)–C(sp 2 ) 偶联，然后是分子内 C–N 键的形成，收率非常好。
• Benzotriazole-Assisted Synthesis of<i>N</i>-(α-Cyanoalkyl)sulfonamides
  作者：Alan R. Katritzky、Daniela C. Oniciu、Ion Ghiviriga

  DOI：10.1080/00397919708004211

  日期：1997.3

  N-(alpha-Benzotriazol-1-ylalkyl)sulfonamides, readily available from benzotriazole, an aldehyde and a sulfonamide, are converted into the corresponding N-(alpha-cyanoalkyl)sulfonamides in good yields by treatment with potassium cyanide.
• The CSIC Reaction on Substrates Derived From Aldehydes
  作者：José L Marco、Simon T Ingate、Carlos Jaime、Ivan Beá

  DOI：10.1016/s0040-4020(00)00124-1

  日期：2000.4

  The Carbanion-mediated Sulfonate (Sulfonamide) Intramolecular Cyclization reaction (CSIC reaction) on conveniently functionalized cyanoalkylsulfonates and cyanoalkylsulfonamides derived from aldehydes is possible and gives the new heterocyclic ring systems 5-alkyl-4-amino-5H-1,2-oxathiole 2,2-dioxide and 3-alkyl-5H-4-amino-5-cyano-5H-2,3-dihydroisothiazole 1,1-dioxide in good yield.

  在方便官能化的氰基烷基磺酸盐和衍生自醛的氰基烷基磺酰胺上进行碳负离子介导的磺酸盐（磺酰胺）分子内环化反应（CSIC反应），可以得到新的杂环体系5-烷基-4-氨基-5 H -1,2-恶唑2 ，2-二氧化物和3-烷基-5 H -4-氨基-5-氰基-5 H -2,3-二氢异噻唑1,1-二氧化物的收率很好。
• Potent and Selective Nonpeptidic Inhibitors of Procollagen C-Proteinase
  作者：Paul V. Fish、Gillian A. Allan、Simon Bailey、Julian Blagg、Richard Butt、Michael G. Collis、Doris Greiling、Kim James、Jackie Kendall、Andrew McElroy、Dawn McCleverty、Charlotte Reed、Robert Webster、Gavin A. Whitlock

  DOI：10.1021/jm061010z

  日期：2007.7.1

  6-Cyclohexyl-N-hydroxy-3-(1,2,4-oxadiazol-5-yl)hexanamides were previously disclosed as inhibitors of procollagen C-proteinase (PCP) culminating in the identification of amide 1. Our objective was to discover a second inhibitor that would have improved affinity for PCP and to optimize properties for transepidermal delivery (TED) to intact skin. Further investigation of this template identified a number of potent PCP inhibitors (IC50 values of 2-6 nM) with improved TED flux. Sulfonamide 56 had excellent PCP enzyme activity when measured with a peptide substrate (K-i 8.7 nM) or with the endogenous substrate procollagen (IC50 3.4 nM) and demonstrates excellent selectivity over MMPs involved in wound healing (> 10 000-fold). In the fibroplasia model, 56 inhibited deposition of insoluble collagen by 76 +/- 2% at 10 mu M and was very effective at penetrating human skin in vitro with a TED flux of 1.5 mu g/cm(2)/h, which compares favorably with values for agents that are known to penetrate skin well in vivo. Based on this profile, 56 (UK-421,045) was selected as a candidate for further preclinical evaluation as a topically applied, dermal anti-scarring agent.