dihydroaustrasulfone alcohol | 1122004-48-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: dihydroaustrasulfone alcohol
• 英文别名: austrasulfone；4-(2-Hydroxyethylsulfonyl)butan-2-one
• CAS: 1122004-48-1
• 化学式: C₆H₁₂O₄S
• 分子量: 180.225
• InChiKey: JWEKXAOPEIZRAR-UHFFFAOYSA-N

物化性质

• 沸点：
  409.8±30.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dihydroaustrasulfone alcohol 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以90%的产率得到austrasulfone
  参考文献：
  名称：

  A neuroprotective sulfone of marine origin and the in vivo anti-inflammatory activity of an analogue

  摘要：

  Our continuing effort of searching bioactive substances from the Formosan soft coral Cladiella australis has led to the isolation of a bioactive substance austrasulfone (1), which possesses significant neuroprotective activities. A straightforward synthesis of 1 was achieved by a two-step reaction sequence. Dihydroaustrasulfone alcohol (3), the synthetic precursor of 1, not only exhibited in vitro anti-inflammatory activity, but also showed potent therapeutic ability in the treatment of neuropathic pain, atherosclerosis, and multiple sclerosis in rats. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.067
• 作为产物：
  描述：

  4-(2-hydroxy-ethylsulfanyl)-butan-2-one 在 间氯过氧苯甲酸 作用下， 生成 dihydroaustrasulfone alcohol
  参考文献：
  名称：

  Inhibitory Effect of Dihydroaustrasulfone Alcohol on the Migration of Human Non-Small Cell Lung Carcinoma A549 Cells and the Antitumor Effect on a Lewis Lung Carcinoma-Bearing Tumor Model in C57BL/6J Mice

  摘要：

  癌症死亡的主要原因有很多，包括癌症转移。从海洋珊瑚中分离出来的二氢澳斯特罗磺醇具有抗氧化活性，但尚未报道其具有抗癌作用。我们首先通过跨孔和伤口愈合实验发现二氢澳斯特拉磺醇对人非小细胞肺癌（NSCLC）A549细胞的迁移和运动具有浓度依赖性的抑制作用。酶谱分析和蛋白质印迹结果表明，二氢澳斯特拉磺醇抑制基质金属蛋白酶（MMP）-2和MMP-9的活性和蛋白表达。进一步研究表明，二氢澳斯特拉砜醇抑制 ERK1/2、p38 和 JNK1/2 的磷酸化。二氢澳大利亚磺醇还抑制 PI3K 的表达和 Akt 的磷酸化。此外，二氢澳斯特拉磺醇显着抑制Lewis肺癌（LLC）小鼠的肿瘤生长。我们的结论是，二氢澳斯特罗砜醇是一种新型纯化合物，具有抗肺癌迁移和抗肿瘤生长活性，未来可能应用于临床治疗。

  DOI：

  10.3390/md12010196

文献信息

• Pharmaceutical uses of sulfur-containing compound
  申请人：NATIONAL SUN YAT-SEN UNIVERSITY

  公开号：US09238620B1

  公开（公告）日：2016-01-19

  The invention relates to uses of the sulfur-containing compound in inhibiting activities of a factor related to cancer metastasis and/or growth. Preferably, the invention relates to uses of the sulfur-containing compound in inhibiting lung cancer metastasis and/or growth.

  本发明涉及使用含硫化合物抑制与癌症转移和/或生长有关的因子的活性。优选地，本发明涉及使用含硫化合物抑制肺癌的转移和/或生长。
• SULFUR-CONTAINING COMPOUND, METHOD OF PREPARATION AND PHARMACEUTICAL USES THEREOF
  申请人：Sheu Jyh-Horng

  公开号：US20090062285A1

  公开（公告）日：2009-03-05

  The invention relates to a sulfur-containing compound and the preparation thereof. The invention also relates to the uses of the sulfur-containing compound in inhibiting inducible nitric oxide synthase and/or cyclooxygenase-2 and in treating the diseases associated with inducible nitric oxide synthase and/or cyclooxygenase-2. This invention also describes a series of chemical analogues of the said sulfur-containing compound and the preparation of these compounds.

  该发明涉及一种含硫化合物及其制备方法。该发明还涉及利用该含硫化合物抑制诱导型一氧化氮合酶和/或环氧合酶-2以及治疗与诱导型一氧化氮合酶和/或环氧合酶-2相关的疾病。该发明还描述了该含硫化合物的一系列化学类似物及这些化合物的制备方法。
• Anti-Restenotic Roles of Dihydroaustrasulfone Alcohol Involved in Inhibiting PDGF-BB-Stimulated Proliferation and Migration of Vascular Smooth Muscle Cells
  作者：Pei-Chuan Li、Ming-Jyh Sheu、Wei-Fen Ma、Chun-Hsu Pan、Jyh-Horng Sheu、Chieh-Hsi Wu

  DOI：10.3390/md13053046

  日期：——

  Dihydroaustrasulfone alcohol (DA), an active compound firstly isolated from marine corals, has been reported to reveal anti-cancer and anti-inflammation activities. These reported activities of DA raised a possible application in anti-restenosis. Abnormal proliferation and migration of vascular smooth muscle cells (VSMCs) and the stimulation of platelet-derived growth factor (PDGF)-BB play major pathological processes involved in the development of restenosis. Experimental results showed that DA markedly reduced balloon injury-induced neointima formation in the rat carotid artery model and significantly inhibited PDGF-BB-stimulated proliferation and migration of VSMCs. Our data further demonstrated that translational and active levels of several critical signaling cascades involved in VSMC proliferation, such as extracellular signal-regulated kinase/ mitogen-activated protein kinases (ERK/MAPK), phosphatidylinositol 3-kinase (PI3K)/AKT, and signal transducer and activator of transcription (STAT), were obviously inhibited. In addition, DA also decreased the activation and expression levels of gelatinases (matrix metalloproteinase (MMP)-2 and MMP-9) involved in cell migration. In conclusion, our findings indicate that DA can reduce balloon injury-neointimal hyperplasia, the effect of which may be modulated through suppression of VSMC proliferation and migration. These results suggest that DA has potential application as an anti-restenotic agent for the prevention of restenosis.

  二氢澳斯特罗磺醇 (DA) 是一种首先从海洋珊瑚中分离出来的活性化合物，据报道具有抗癌和抗炎活性。这些报道的 DA 活性提出了在抗再狭窄方面的可能应用。血管平滑肌细胞（VSMC）的异常增殖和迁移以及血小板衍生生长因子（PDGF）-BB的刺激在再狭窄的发展中发挥着主要的病理过程。实验结果表明，DA 显着减少大鼠颈动脉模型中球囊损伤诱导的新内膜形成，并显着抑制 PDGF-BB 刺激的 VSMC 增殖和迁移。我们的数据进一步表明，参与 VSMC 增殖的几个关键信号级联的翻译和活性水平，例如细胞外信号调节激酶/丝裂原激活蛋白激酶 (ERK/MAPK)、磷脂酰肌醇 3-激酶 (PI3K)/AKT 和信号转导子和转录激活子（STAT）均受到明显抑制。 此外，DA还降低了参与细胞迁移的明胶酶（基质金属蛋白酶（MMP）-2和MMP-9）的激活和表达水平。总之，我们的研究结果表明，DA 可以减少球囊损伤 - 新生内膜增生，其作用可能通过抑制 VSMC 增殖和迁移来调节。 这些结果表明DA具有作为抗再狭窄剂来预防再狭窄的潜在应用。
• TW2016/1713
  申请人：——

  公开号：——

  公开（公告）日：——
• Sulfur-containing compound, method of preparation and pharmaceutical uses thereof
  申请人：National Sun Yat-Sen University

  公开号：EP2030968B1

  公开（公告）日：2017-02-22