2-(N-(2-oxopropyl)methylsulfonamido)acetic acid | 852960-76-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(N-(2-oxopropyl)methylsulfonamido)acetic acid
• 英文别名: [(Methylsulfonyl)(2-oxopropyl)amino]acetic acid；2-[methylsulfonyl(2-oxopropyl)amino]acetic acid
• CAS: 852960-76-0
• 化学式: C₆H₁₁NO₅S
• mdl: MFCD24485275
• 分子量: 209.223
• InChiKey: XUAFDWBIPCRPFT-UHFFFAOYSA-N

物化性质

• 沸点：
  395.9±52.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(N-(2-oxopropyl)methylsulfonamido)acetic acid 在 盐酸 、 氯化铵 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis

  摘要：

  A set of structurally diverse N-amino delta-lactams decorated with a 5-nitro-2-furyl moiety was synthesized using isocyanide-based multicomponent chemistry and evaluated for antibacterial activity. Three compounds displayed a selective and potent (MIC 22-33 mu M) inhibition of M. tuberculosis H(37)Rv strain growth, while other Gram-positive (MRSA and E. faecium) or Gram-negative (E. coli, P. aeruginosa, A. baumannii, K. pneumoniae) pathogens were not affected. The compounds also displayed moderate low cytotoxicity, as demonstrated in cell line viability assays. Several multidrug-and poly-resistant patient-derived M. tuberculosis strains were found to be susceptible to treatment with these compounds. The three most potent compounds share a significant structural similarity which provides a basis for further scaffold-hopping analog design. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.003
• 作为产物：
  描述：

  N-(甲基磺酰基)甘氨酸 、 一氯丙酮 在 18-冠醚-6 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以21.3 g的产率得到2-(N-(2-oxopropyl)methylsulfonamido)acetic acid
  参考文献：
  名称：

  New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis

  摘要：

  A set of structurally diverse N-amino delta-lactams decorated with a 5-nitro-2-furyl moiety was synthesized using isocyanide-based multicomponent chemistry and evaluated for antibacterial activity. Three compounds displayed a selective and potent (MIC 22-33 mu M) inhibition of M. tuberculosis H(37)Rv strain growth, while other Gram-positive (MRSA and E. faecium) or Gram-negative (E. coli, P. aeruginosa, A. baumannii, K. pneumoniae) pathogens were not affected. The compounds also displayed moderate low cytotoxicity, as demonstrated in cell line viability assays. Several multidrug-and poly-resistant patient-derived M. tuberculosis strains were found to be susceptible to treatment with these compounds. The three most potent compounds share a significant structural similarity which provides a basis for further scaffold-hopping analog design. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.003

文献信息

• Cyclic products of the Ugi reaction of aldehydo and keto carboxylic acids: chemoselective modification
  作者：Alan Tsaloev、Alexei Ilyin、Sergey Tkachenko、Alexandre Ivachtchenko、Dmitry Kravchenko、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2011.02.028

  日期：2011.4

  A method for the chemoselective reduction of Ugi-type lactam amides at the lactam carbonyl functionality with borane complexes has been developed. The novel reduction products can be further manipulated synthetically to yield various novel N- and C-terminally active unnatural amino acid building blocks.

  已经开发了一种用硼烷配合物在内酰胺羰基官能团上化学选择性还原Ugi型内酰胺酰胺的方法。新型还原产物可以进一步合成处理以产生各种新型的N-和C-末端活性的非天然氨基酸构件。
• Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines
  作者：Mikhail Krasavin、Vladislav Parchinsky、Alexei Shumsky、Igor Konstantinov、Anton Vantskul

  DOI：10.1016/j.tetlet.2009.12.141

  日期：2010.3

  A four-center, three-component Ugi-type reaction of a variety of keto acids, Boc- or Cbz-protected hydrazine, and isocyanides offers a simple and high yielding access to cyclic products containing an N-aminolactam unit. The latter are shown to form consistently an intramolecular hydrogen bond leading to a p-turn-like secondary structure. The possibility of integrating such N-aminolactam units (without disruption of the folded structure) into pseudotripeptide fragments is demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
• New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis
  作者：Mikhail Krasavin、Vladislav Parchinsky、Grigory Kantin、Olga Manicheva、Marine Dogonadze、Tatiana Vinogradova、Bianka Karge、Mark Brönstrup

  DOI：10.1016/j.bmc.2017.02.003

  日期：2017.3

  A set of structurally diverse N-amino delta-lactams decorated with a 5-nitro-2-furyl moiety was synthesized using isocyanide-based multicomponent chemistry and evaluated for antibacterial activity. Three compounds displayed a selective and potent (MIC 22-33 mu M) inhibition of M. tuberculosis H(37)Rv strain growth, while other Gram-positive (MRSA and E. faecium) or Gram-negative (E. coli, P. aeruginosa, A. baumannii, K. pneumoniae) pathogens were not affected. The compounds also displayed moderate low cytotoxicity, as demonstrated in cell line viability assays. Several multidrug-and poly-resistant patient-derived M. tuberculosis strains were found to be susceptible to treatment with these compounds. The three most potent compounds share a significant structural similarity which provides a basis for further scaffold-hopping analog design. (C) 2017 Elsevier Ltd. All rights reserved.