3-acetamido-4,4-dimethylthietan-2-one | 88168-59-6

• 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: 3-acetamido-4,4-dimethylthietan-2-one
• 英文别名: (3R)-3-acetamido-4,4-dimethylthietan-2-one；N-[(3R)-2,2-dimethyl-4-oxothietan-3-yl]acetamide
• CAS: 88168-59-6
• 化学式: C₇H₁₁NO₂S
• 分子量: 173.236
• InChiKey: LFIQZXJVBJYDNW-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetamido-4,4-dimethylthietan-2-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以63%的产率得到N-乙酰基-D-青霉胺
  参考文献：
  名称：

  Al-Zaidi, Shakir M.R.; Crilley, Martine M. L.; Stoodley, Richard J., Journal of the Chemical Society. Perkin transactions I, 1983, p. 2259 - 2266

  摘要：

  DOI：
• 作为产物：
  描述：

  D-青霉胺 在 吡啶 、 乙酸酐 作用下， 反应 15.0h， 以24%的产率得到3-acetamido-4,4-dimethylthietan-2-one
  参考文献：
  名称：

  Moynihan, Humphrey A.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 797 - 806

  摘要：

  DOI：

文献信息

• Synthesis and nitric oxide releasing properties of novel fluoro<i>S</i>-nitrosothiols
  作者：Yang Zhou、Jinyi Tan、Yuping Dai、Yanmin Yu、Qi Zhang、Mark E. Meyerhoff

  DOI：10.1039/c8cc08868c

  日期：——

  series of new fluoro S-nitrosothiols is reported as potential nitric oxide (NO) donors. A three-step synthesis and the NO releasing kinetic profiles of these species are presented. The stoichiometric release of NO, with the clean formation of corresponding disulfides, confirms that these new species can facilitate their application as NO donors for various applications including creating novel antimicrobial

  据报道，一系列新的氟 S-亚硝基硫醇是潜在的一氧化氮 (NO) 供体。介绍了这些物质的三步合成和 NO 释放动力学曲线。NO 的化学计量释放以及相应二硫化物的干净形成，证实这些新物种可以促进它们作为 NO 供体用于各种应用，包括创建新型抗菌和抗血栓的基于含氟聚合物的医疗设备。
• Glutathione Responsive β-Cyclodextrin Conjugated S-Nitrothiols as a Carrier for Intracellular Delivery of Nitric Oxide
  作者：Fan Jia、Yongyan Deng、Yu Fang、Qiao Jin、Jian Ji

  DOI：10.1021/acs.bioconjchem.8b00735

  日期：2019.3.20

  Nitric oxide (NO) exerts multiple functions in many life processes and was of great significance in a variety of biomedical scenarios. However, the mismatches between releasing locations and NO active sites seriously limited the available NO at areas of interest and greatly dampen the overall efficiency of delivery systems. Therefore, in the present study, a NO donor was developed to achieve intracellular delivery and release of NO to overcome the aforementioned challenges. Enhanced uptake and effective intracellular release of NO were realized via β-cyclodextrin (β-CD) mediated endocytosis and high level glutathione (GSH) inside cells, respectively. We demonstrated that intracellularly delivered NO would exert stronger bioeffects than premature release of NO outside targeted cells. Besides, β-CD assisted cellular uptake proved indispensable in maximizing the influence of NO in modulating cellular behavior. These results demonstrated the significance of intracellular delivery and release of NO in improving its bioutilization. The carrier could efficiently inhibit proliferation of SMCs, while promoting the growth of ECs. Such cell-type-differed physiological effects were advantageous in re-endothelialization and might hold great potential in cardiovascular applications.

  一氧化氮（NO）在许多生命过程中发挥多种功能，在各种生物医学场景中具有重要意义。然而，释放位置和NO活性位点之间的不匹配严重限制了感兴趣区域的可用NO，并极大地降低了传递系统的整体效率。因此，在本研究中，开发了NO供体来实现NO的细胞内递送和释放，以克服上述挑战。分别通过细胞内β-环糊精（β-CD）介导的内吞作用和高水平谷胱甘肽（GSH）实现NO的增强摄取和有效的细胞内释放。我们证明，细胞内递送的 NO 比在靶细胞外过早释放 NO 会产生更强的生物效应。此外，β-CD 辅助细胞摄取被证明对于最大化 NO 在调节细胞行为中的影响是不可或缺的。这些结果证明了细胞内递送和释放NO对于提高其生物利用度的重要性。该载体能够有效抑制SMCs的增殖，同时促进ECs的生长。这种细胞类型不同的生理效应有利于再内皮化，并且可能在心血管应用中具有巨大潜力。
• Synthesis and vasorelaxant properties of hybrid molecules out of NO-donors and the β-receptor blocking drug propranolol
  作者：Michael Decker、Andreas König、Erika Glusa、Jochen Lehmann

  DOI：10.1016/j.bmcl.2004.07.014

  日期：2004.10

  S-Nitroso-N-acetylpenicillamine (SNAP) and 3-nitrooxypivaloyl acid were combined in the form of the respective amides with propranolol, in order to obtain prodrugs (NO-propranololes) with beta-receptor blocking properties of the latter compound with nitric oxide releasing properties of the former compounds. A respective nitratoester could not be synthesized, because it immediately rearranges to the amide after deprotection of the amino group. In vitro tests on porcine pulmonary arteries showed that both types of hybrid molecules (6, 12) elicited vasorelaxation, but the nitratoamide was less potent by more than one order of magnitude. The vasorelaxant effect of SNAP was more pronounced than that of the SNAP-hybrid (12), on the other hand the nitratoamide 6 was more potent than 3-nitrooxypivaloyl acid. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxicities of mannose conjugated S -Nitroso- N -acetylpenicillamine (SNAP)
  作者：Xuejun Wu、Xiaoping Tang、Ming Xian、Paul G. Brauschweiger、Peng George Wang

  DOI：10.1016/s0968-0896(02)00064-0

  日期：2002.7

  A series of mannose conjugated S-nitroso-N-acetylpenicillamines (SNAPs) has been synthesized, and their cytotoxicities were assessed for DU 145 human prostate cancer cells and Hela R cancer cells. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Glyco-S-nitrosothiols, a novel class of no donor compounds
  作者：Johnny Ramirez、Libing Yu、Jun Li、Paul G. Braunschweiger、Peng George Wang

  DOI：10.1016/0960-894x(96)00484-2

  日期：1996.11

  Three novel glyco-S-nitrosothiol NO donor compounds 1, 2, and 3 have been synthesized. These compounds outperform S-nitroso-N-acetylpenicillamine (SNAP) in aqueous solubility and stability, with and without EDTA and in the presence or absence of Cu2+. Copyright (C) 1996 Elsevier Science Ltd