tetradecyl propargyl ether | 1097190-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetradecyl propargyl ether
• 英文别名: 1-Prop-2-ynoxytetradecane；1-prop-2-ynoxytetradecane
• CAS: 1097190-17-4
• 化学式: C₁₇H₃₂O
• 分子量: 252.44
• InChiKey: LHXBKOWHWJBSHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(乙酰氧基甲基)-6-叠氮基四氢-2H-吡喃-3,4,5-三基三乙酸酯 、 tetradecyl propargyl ether 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 12.0h， 以91%的产率得到
  参考文献：
  名称：

  Triazole-Linked Glycolipids Enhance the Susceptibility of MRSA to β-Lactam Antibiotics

  摘要：

  We show here that a series of triazolyl glycolipid derivatives modularly synthesized by a "click" reaction have the ability to increase the susceptibility of a drug-resistant bacterium to beta-lactam antibiotics. We determine that the glycolipids can suppress the minimal inhibitory concentration of a number of ineffective beta-lactams, upward of 256-fold, for methicillin-resistant Staphylococuss aureus (MRSA). The mechanism of action has been preliminarily probed and discussed.

  DOI：

  10.1021/acsmedchemlett.5b00142

文献信息

• Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Brendan L. Wilkinson、Hilary Long、Edith Sim、Antony J. Fairbanks

  DOI：10.1016/j.bmcl.2008.09.082

  日期：2008.12

  A series of arabino glycosyl triazoles with varying hydrophobic groups were synthesised as putative mimics of decaprenolphosphoarabinose (DPA) as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity, with strong dependence on the identity of the hydrophobic side chain.

  合成了一系列具有不同疏水基团的阿拉伯糖基三唑，作为癸癸醇磷酸阿拉伯糖（DPA）的假定模拟物，作为分枝杆菌细胞壁生物合成的潜在抑制剂。针对牛分枝杆菌BCG的生物学测试表明，分枝杆菌活性低至中度，强烈依赖疏水性侧链的身份。
• [EN] LIPOPHOSPHONOXINS OF SECOND GENERATION, AND THEIR USE<br/>[FR] LIPOPHOSPHONOXINES DE SECONDE GÉNÉRATION ET LEUR UTILISATION
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR V V I

  公开号：WO2017186200A1

  公开（公告）日：2017-11-02

  Lipophosphonoxins of general Formula I are described here, wherein R1 is C8-C22, preferably C10-C18 and more preferably C12-C16 alkyl, or hexadecyloxypropyl, tetradecyloxypropyl, tetradecyloxyethyl or hexadecyloxyethyl, R2 is uracil, thymine, or cytosine, R3 is selected from a group which contains compounds of general formulas II and III, wherein R4 is H, CH2OH or CH2NH2, R5 is H, OH or NH2, R6 is H, OH or NH2, R7 is H, CH2OH or CH2NH2, wherein at least one of the groups R5 and R6 must be NH2 or one of the groups R4 and R7 must be CH2NH2. R8 is H, CH2OH or CH2NH2, R9 is H, OH or NH2, R10 is H, OH or NH2, R11 is H, OH or NH2, R12 is H, CH2OH or CH2NH2, wherein at least one of the groups R9, R10 and R11 must be NH2 or one of the groups R8 a R12 must be CH2NH2. R13 is NH2 or NH-CH(NH2)NH, R14 is NH2 or NH-CH(NH2)NH, R15 is NH2 or NH-CH(NH2)NH, R16 is NH2 or NH-CH(NH2)NH. Further, diastereomers and mixtures of diastereomers of compounds of general formula I and the corresponding pharmaceutically acceptable salts and/or hydrates are described. The compounds of general formula I are useful as antibacterial agents or active ingredients in disinfectants, and/or of selective in vitro culture media.

  本文描述了一般式I的脂肪磷酸诺酮，其中R1为C8-C22，优选为C10-C18，更优选为C12-C16烷基，或十六烷氧基丙基，十四烷氧基丙基，十四烷氧基乙基或十六烷氧基乙基，R2为尿嘧啶，胸腺嘧啶或胞嘧啶，R3从一组化合物中选择，该组化合物包含一般式II和III，其中R4为H，CH2OH或CH2NH2，R5为H，OH或NH2，R6为H，OH或NH2，R7为H，CH2OH或CH2NH2，其中R5和R6中至少有一个必须为NH2，或者R4和R7中的一个必须为CH2NH2。R8为H，CH2OH或CH2NH2，R9为H，OH或NH2，R10为H，OH或NH2，R11为H，OH或NH2，R12为H，CH2OH或CH2NH2，其中R9、R10和R11中至少有一个必须为NH2，或者R8和R12中的一个必须为CH2NH2。R13为NH2或NH-CH（NH2）NH，R14为NH2或NH-CH（NH2）NH，R15为NH2或NH-CH（NH2）NH，R16为NH2或NH-CH（NH2）NH。此外，还描述了一般式I的对映异构体和对应的药学上可接受的盐和/或水合物的混合物。一般式I的化合物可用作抗菌剂或消毒剂的活性成分和/或体外选择性培养基。
• LIPOPHOSPHONOXINS OF SECOND GENERATION, AND THEIR USE
  申请人：Ustav organicke chemie a biochemie AV CR, v.v.i.

  公开号：EP3448865B1

  公开（公告）日：2019-09-04
• [EN] NANOFIBROUS MATERIAL PARTICULARLY FOR TOPICAL USE IN THERAPIES<br/>[FR] MATÉRIAU NANOFIBREUX DESTINÉ EN PARTICULIER À UNE UTILISATION TOPIQUE DANS DES THÉRAPIES
  申请人：UNIV KARLOVA

  公开号：WO2021244684A1

  公开（公告）日：2021-12-09

  The invention discloses nanofibrous material particularly for topical use in therapies consisting of compound chosen from a group comprising lipophosphonoxins of general formula I, wherein R1 is (C8–C22)alkyl, hexadecyloxypropyl, tetradecyloxypropyl, tetradecyloxyethyl, or hexadecyloxyethyl, R2 is uracil, thymine, or cytosine, and R3 is primary, secondary, or tertiary amine, diastereomers and mixtures of diastereomers of compounds according to formula I, and their pharmaceutically acceptable salts and hydrates, incorporated into polyester-based nanofibers of general formula II, wherein m has a value of at least 1, and R is -H or (C1–C10)alkyl, or copolymers thereof.
• Triazole-Linked Glycolipids Enhance the Susceptibility of MRSA to β-Lactam Antibiotics
  作者：Xi-Le Hu、Dan Li、Lei Shao、Xiaojing Dong、Xiao-Peng He、Guo-Rong Chen、Daijie Chen

  DOI：10.1021/acsmedchemlett.5b00142

  日期：2015.7.9

  We show here that a series of triazolyl glycolipid derivatives modularly synthesized by a "click" reaction have the ability to increase the susceptibility of a drug-resistant bacterium to beta-lactam antibiotics. We determine that the glycolipids can suppress the minimal inhibitory concentration of a number of ineffective beta-lactams, upward of 256-fold, for methicillin-resistant Staphylococuss aureus (MRSA). The mechanism of action has been preliminarily probed and discussed.