3-azidopropanthiol | 1260247-53-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-azidopropanthiol
• 英文别名: 3-azidopropanethiol；3-azidopropane-1-thiol
• CAS: 1260247-53-7
• 化学式: C₃H₇N₃S
• 分子量: 117.175
• InChiKey: IOIXFIGYRISONS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-azidopropanthiol 、 20-ethynyl-19-deschloransamitocin P-3 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 40.0h， 以0.7 mg的产率得到
  参考文献：
  名称：

  通过变位合成制备新型炔烃修饰的安丝菌素。

  摘要：

  描述了通过用炔烃取代的氨基苯甲酸对 Actinosynnema pretiosum 突变体进行突变补充来制备炔烃修饰的安丝菌素。这种修饰为通过 Huisgen 型环加成引入硫醇接头铺平了道路，该环加成主要可用于产生肿瘤靶向缀合物。在生物活性测试中，只有那些在 C-3 处带有酯侧链的新型安丝菌素衍生物表现出很强的抗增殖活性。

  DOI：

  10.3762/bjoc.10.49
• 作为产物：
  描述：

  3-氯-1-丙硫醇 在 sodium azide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以75%的产率得到3-azidopropanthiol
  参考文献：
  名称：

  Introduction of various functionalities into polysaccharides using alkynyl ethers as precursors: Pentynyl dextrans

  摘要：

  Following the concept of using O-alkynyl glycans as key precursors of functional polysaccharides. dextran derivatives with nearly the same distritbution pattern, but various functional groups - for common (bio)conjugation reactions, molecular recognition, and antioxidant activity - have been prepared. Pentynyl dextran well characterized with respect to the degree of substitution (DS 0.43) and the distribution of alkynyl groups to the various OH of the glucosyl unit, was further modified by 1,3-dipolar cycloaddition of various functionalized azides, thus introducing amino, hydroxy, thiol, and carboxyl groups with good to quantitative yield. Besides these functional groups, biotin and tocopherol were introduced with about 60% conversion of alkyne groups. Biotinylated dextran was demonstrated to bind specifically to fluorophor-labeled streptavidin, while glucose linked tocopherol did not show loss of antioxidant activity. Formation of triazole derivatives was proved by ATR-IR and NMR spectroscopy, and after methanolysis of the dextran, by ESI mass spectrometry. Degree of conversion was estimated from H-1 NMR spectra, decrease of pentynyl groups in the product mixture analyzed by GLC, and elemental analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2011.11.082

文献信息

• Discovery of Potent and Fast-Acting Antimalarial Bis-1,2,4-triazines
  作者：Daniel L. Priebbenow、Mitch Mathiew、Da-Hua Shi、Jitendra R. Harjani、Julia G. Beveridge、Marina Chavchich、Michael D. Edstein、Sandra Duffy、Vicky M. Avery、Robert T. Jacobs、Stephen Brand、David M. Shackleford、Wen Wang、Longjin Zhong、Given Lee、Erin Tay、Helena Barker、Elly Crighton、Karen L. White、Susan A. Charman、Amanda De Paoli、Darren J. Creek、Jonathan B. Baell

  DOI：10.1021/acs.jmedchem.1c00044

  日期：2021.4.8

  potent in vitro activity against Plasmodium falciparum parasites were recently discovered. To improve the pharmacokinetic properties of the triazine derivatives, a new structure–activity relationship (SAR) investigation was initiated with a focus on enhancing the metabolic stability of lead compounds. These efforts led to the identification of second-generation highly potent antimalarial bis-triazines

  最近发现了新型 3,3'-二取代-5,5'-双（1,2,4-三嗪）化合物，具有有效的体外抗恶性疟原虫寄生虫的活性。为了改善三嗪衍生物的药代动力学特性，启动了一项新的构效关系（SAR）研究，重点是增强先导化合物的代谢稳定性。这些努力导致了第二代高效抗疟药双三嗪的鉴定，以三嗪23为例，其体外代谢稳定性显着改善（人和小鼠肝微粒体中的蛋白质为 8 和 42 μL/min/mg）。在 Peters 4 天试验中，还观察到二取代三嗪二聚体23可以抑制寄生虫血症，平均 ED 50值为 1.85 mg/kg/天，并表现出快速杀灭特性，揭示了一类新型口服抗疟化合物兴趣。
• Light‐Sensitive Phenacyl Crosslinked Dextran Hydrogels for Controlled Delivery**
  作者：Tobias G. Brevé、Mike Filius、Sven Weerdenburg、Stefan J. van der Griend、Tim P. Groeneveld、Antonia G. Denkova、Rienk Eelkema

  DOI：10.1002/chem.202103523

  日期：2022.2.19

  Polymer phenacyl crosslinked hydrogels that can release doxorubicin, bovine serum albumin and immunoglobulin G by using light (254 nm–375 nm) as a trigger are reported. One crosslinker was designed to optimize the overlap with the Cerenkov luminescence emission window, bearing an π-extended phenacyl core, resulting in a high quantum yield (QY, 14 %) of photocleavage when irradiated with 375 nm light.

  据报道，聚合物苯甲酰交联水凝胶可以通过光（254 nm-375 nm）作为触发剂释放阿霉素、牛血清白蛋白和免疫球蛋白 G。一种交联剂旨在优化与切伦科夫发光发射窗口的重叠，具有 π 延伸的苯甲酰核，在 375 nm 光照射下产生高量子产率（QY，14%）的光裂解。
• Reactions in Elastomeric Nanoreactors Reveal the Role of Force on the Kinetics of the Huisgen Reaction on Surfaces
  作者：Xu Han、Shudan Bian、Yong Liang、K. N. Houk、Adam B. Braunschweig

  DOI：10.1021/ja504137u

  日期：2014.7.30

  The force dependence of the copper-free Huisgen cycloaddition between an alkyne and a surface-bound azide was examined in elastomeric nanoreactors. These studies revealed that pressure and chain length are critical factors that determine the reaction rate. These experiments demonstrate the central role of pressure and surface structure on interfacial processes that are increasingly important in biology, materials science, and nanotechnology.
• Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules
  作者：Wei Chen、Shengqiang Shen、Lili Dong、Jianjun Zhang、Qing Yang

  DOI：10.1016/j.bmc.2017.11.042

  日期：2018.1

  To develop selective inhibitors for beta-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl-naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity against glycosyl hydrolase family 20 and 84 (GH20 and GH84) beta-N-acetylhexosaminidases. These compounds which incorporate groups with varied sizes and lengths at the linker region between thioglycosyl moiety and naphthalimide moiety are designed to improve the selectivity and stacking interactions. The GH84 human O-GlcNAcase (hOGA) was sensitive to the subtle changes in the linker region and the optimal choice is a small size linker with six atoms length. And the GH20 insect beta-N-acetylhexosaminidase OfHex1 could tolerate compounds with a hydrophobic bulky linker. Especially, the compound 5c (hOGA, K-i = 3.46 mu M; OfHex1, K-i > 200 mu M) and the compound 6f (hOGA, K-i > 200 mu M; OfHex1, K-i = 21.81 mu M) displayed high selectivity. The molecular docking results indicated that the inhibition mechanism was different between the two families due to their different structural characteristics beyond the active sites. These results provide some promising clues to improve selectivity of potent molecules against beta-N-acetylhexosaminidases. (C) 2017 Elsevier Ltd. All rights reserved.
• Introduction of various functionalities into polysaccharides using alkynyl ethers as precursors: Pentynyl dextrans
  作者：M. Nazir Tahir、Nico Lämmerhardt、Petra Mischnick

  DOI：10.1016/j.carbpol.2011.11.082

  日期：2012.3

  Following the concept of using O-alkynyl glycans as key precursors of functional polysaccharides. dextran derivatives with nearly the same distritbution pattern, but various functional groups - for common (bio)conjugation reactions, molecular recognition, and antioxidant activity - have been prepared. Pentynyl dextran well characterized with respect to the degree of substitution (DS 0.43) and the distribution of alkynyl groups to the various OH of the glucosyl unit, was further modified by 1,3-dipolar cycloaddition of various functionalized azides, thus introducing amino, hydroxy, thiol, and carboxyl groups with good to quantitative yield. Besides these functional groups, biotin and tocopherol were introduced with about 60% conversion of alkyne groups. Biotinylated dextran was demonstrated to bind specifically to fluorophor-labeled streptavidin, while glucose linked tocopherol did not show loss of antioxidant activity. Formation of triazole derivatives was proved by ATR-IR and NMR spectroscopy, and after methanolysis of the dextran, by ESI mass spectrometry. Degree of conversion was estimated from H-1 NMR spectra, decrease of pentynyl groups in the product mixture analyzed by GLC, and elemental analysis. (C) 2011 Elsevier Ltd. All rights reserved.