methyl 2-((3-hydroxypropyl)thio)acetate | 132767-71-6

• 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: methyl 2-((3-hydroxypropyl)thio)acetate
• 英文别名: methyl 2-(3-hydroxypropylsulfanyl)acetate
• CAS: 132767-71-6
• 化学式: C₆H₁₂O₃S
• mdl: MFCD12144060
• 分子量: 164.225
• InChiKey: GAIVHBQWSDJAQW-UHFFFAOYSA-N

物化性质

• 沸点：
  237.3±20.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-((3-hydroxypropyl)thio)acetate 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 2-(3-(trityloxy)propylsulfonyl)acetate
  参考文献：
  名称：

  Vinyl sulfone analogs of lysophosphatidylcholine irreversibly inhibit autotaxin and prevent angiogenesis in melanoma

  摘要：

  Autotaxin (ATX) is an enzyme discovered in the conditioned medium of cultured melanoma cells and identified as a protein that strongly stimulates motility. This unique ectonucleotide pyrophosphatase and phosphodiesterase facilitates the removal of a choline headgroup from lysophosphatidylcholine (LPC) to yield lysophosphatidic acid (LPA), which is a potent lipid stimulator of tumorigenesis. Thus, ATX has received renewed attention because it has a prominent role in malignant progression with significant translational potential. Specifically, we sought to develop active site-targeted irreversible inhibitors as anti-cancer agents. Herein we describe the synthesis and biological activity of an LPC-mimetic electrophilic affinity label that targets the active site of ATX, which has a critical threonine residue that acts as a nucleophile in the lysophospholipase D reaction to liberate choline. We synthesized a set of quaternary ammonium derivative-containing vinyl sulfone analogs of LPC that function as irreversible inhibitors of ATX and inactivate the enzyme. The analogs were tested in cell viability assays using multiple cancer cell lines. The IC50 values ranged from 6.74 to 0.39 mu M, consistent with a K-i of 3.50 mu M for inhibition of ATX by the C16H33 vinyl sulfone analog CVS-16 (10b). A phenyl vinyl sulfone control compound, PVS-16, lacking the choline-like quaternary ammonium mimicking head group moiety, had little effect on cell viability and did not inhibit ATX. Most importantly, CVS-16 (10b) significantly inhibited melanoma progression in an in vivo tumor model by preventing angiogenesis. Taken together, this suggests that CVS-16 (10b) is a potent and irreversible ATX inhibitor with significant biological activity both in vitro and in vivo. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.054
• 作为产物：
  描述：

  3-巯基-1-丙醇 、 溴乙酸甲酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以93%的产率得到methyl 2-((3-hydroxypropyl)thio)acetate
  参考文献：
  名称：

  [EN] BORONIC ACID DERIVATIVES
  [FR] DÉRIVÉS D'ACIDE BORONIQUE

  摘要：

  本发明涉及α-氨基硼酸衍生物。这些化合物对抑制免疫蛋白酶体(LMP7)的活性以及治疗和/或预防受免疫蛋白酶体活性影响的医疗状况，如炎症性和自身免疫疾病、神经退行性疾病、增殖性疾病和癌症，具有用处。

  公开号：

  WO2020020858A1

文献信息

• Synthesis and pharmacological properties of N-(3-{3-(1-piperidinylmethyl)phenoxy}propyl)-2-(2-hydroxyethylthio)acetamide and related compounds as antiulcer agents. I.
  作者：Ikuo UEDA、Katsuyuki ISHII、Katsuo SHINOZAKI、Masao SEIKI、Heihachiro ARAI、Minoru HATANAKA

  DOI：10.1248/cpb.38.3035

  日期：——

  N-Phenoxypropylacetamide derivatives were prepared and tested for antiulcer activity. These compounds exhibited both gastric acid antisecretory and cytoprotective properties. Structure-activity studies led to the identification of N-[3-(3-(1-piperidinylmethyl)phenoxy)propyl]-2-(2-hydroxyethylt hio)acetamide (8), which was selected for further development and clinical evaluation.

  制备了N-苯氧基丙基乙酰胺衍生物，并测试了其抗溃疡活性。这些化合物显示出胃酸的抗分泌和细胞保护性能。结构活性研究导致鉴定出N- [3-（3-（1-（哌啶基甲基甲基）苯氧基）丙基] -2-（2-羟乙基硫代）乙酰胺（8），该化合物被选作进一步开发和临床评估。
• Visible-Light-Mediated Thiol–Ene Reactions through Organic Photoredox Catalysis
  作者：Gaoyuan Zhao、Sarbjeet Kaur、Ting Wang

  DOI：10.1021/acs.orglett.7b01441

  日期：2017.6.16

  Synthetically useful radical thiol–ene reactions can be initiated by visible-light irradiation in the presence of an organic photocatalyst, 9-mesityl-10-methylacridinum tetrafluoroborate. The key thiyl radical intermediates are generated upon quenching of the photoexcited catalyst with a variety of thiols. The success of this method requires only the use of near-stoichiometric levels of alkene coupling

  在有机光催化剂9-间苯甲基-10-甲基ac啶四氟硼酸盐的存在下，可见光辐射可引发合成上有用的自由基硫醇-烯反应。关键的巯基自由基中间体是在光激发的催化剂上用各种硫醇淬灭后生成的。该方法的成功仅需要使用接近化学计量水平的烯烃偶联配偶体。使用这些高效的无金属条件，碳水化合物和多肽之间的硫醇-烯反应可以实现出色的收率。
• Metal-free photocatalytic thiol–ene/thiol–yne reactions
  作者：Sarbjeet Kaur、Gaoyuan Zhao、Evan Busch、Ting Wang

  DOI：10.1039/c8ob02313a

  日期：——

  presence of visible light is used to initiate thiol–ene and thiol–yne reactions. Thiyl radicals are generated upon quenching the photoexcited catalyst with a range of thiols. The highlighted mild nature of the reaction conditions allows a broad substrate scope of the reactants. Relying on this efficient metal-free condition, both thiol–ene and thiol–yne reactions between carbohydrates and peptides could

  在可见光的存在下，使用有机光催化剂（9-甲磺酰-10-甲基ac啶四氟硼酸酯）引发硫醇-烯和硫醇-炔反应。通过用一定范围的硫醇淬灭光激发的催化剂后会生成巯基。反应条件突出的温和性质允许反应物的广泛的底物范围。依靠这种有效的无金属条件，碳水化合物和多肽之间的硫醇-烯和硫醇-炔反应都可以实现极高的收率。
• CEDA, IKUO;ISHII, KATSUYUKI;SHINOZAKI, KATSUO;SEIKI, MASAO;ARAI, HEIHACHI+, CHEM. AND PHARM. BULL., 38,(1990) N1, C. 3035-3041
  作者：CEDA, IKUO、ISHII, KATSUYUKI、SHINOZAKI, KATSUO、SEIKI, MASAO、ARAI, HEIHACHI+

  DOI：——

  日期：——
• BORONIC ACID DERIVATIVES
  申请人：Merck Patent GmbH

  公开号：EP3826723A1

  公开（公告）日：2021-06-02