(2R)-1,2,3-propanetriol 1-(methylsulfonate) ester | 53901-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2R)-1,2,3-propanetriol 1-(methylsulfonate) ester
• 英文别名: (R)-3-methanesulfonyloxy-propane-1,2-diol；(R)-3-Methansulfonyloxy-propan-1,2-diol；(R)-O¹-Methansulfonyl-glycerin；[(2R)-2,3-dihydroxypropyl] methanesulfonate
• CAS: 53901-53-4
• 化学式: C₄H₁₀O₅S
• 分子量: 170.186
• InChiKey: KHKXPBTUCRNATA-SCSAIBSYSA-N

物化性质

• 沸点：
  78-79 °C(Press: 0.2 Torr)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-1,2,3-propanetriol 1-(methylsulfonate) ester 、 2'4'-二氟-2-[1-(1H-1,2,4-三唑基)]苯乙酮 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+)-(2R)-cis-2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol methanesulfonate ester
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Structure−Activity Relationships of Novel Antifungal Triazoles for Dermatology

  摘要：

  In search for new compounds with potential for clinical use as antifungal agents in dermatology, a series of 12 azole compounds were synthesized stereospecifically and investigated specifically for their activity against dermatophyte fungal infections in animal models. This panel of azoles was studied in vitro and compared with itraconazole and terbinafine for their antifungal activity using a panel of 24 Candida spp. and 182 dermatophyte isolates. Three azoles (1c, 2c, and 4c) showed in vitro antifungal potency equivalent to itraconazole, but superior to terbinafine, against a panel of 24 Candida spp. with comparable or lower activity than that of itraconazole and terbinafine against 182 dermatophyte isolates and only rare activity against other pathogenic fungi. However, in vivo 1c and 4c, both given orally, demonstrated antifungal activity at least three times greater than itraconazole and were superior compared to terbinafine in M. cants infected guinea pigs. In a mouse model infected by T mentagrophytes, again 4c, but not 1c, showed 5-fold superior activity over itraconazole and terbinafine. Compound 2c was effective in both models but less effective than itraconazole in these models. On the basis of these promising results, 4c is currently being clinically investigated for its potential as a novel antifungal agent against dermatophytosis.

  DOI：

  10.1021/jm0494772
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 (2R)-1,2,3-propanetriol 1-(methylsulfonate) ester
  参考文献：
  名称：

  I. MESYL ESTERS OF GLYCEROL

  摘要：

  本文描述了L-α-monomesylin、D-α,β-dimesylin和DL-α,β-dimesylin、trimesylin的合成方法，并报告了它们的一些物理性质。观察到L-α-monomesylin和D-α,β-dimesylin在吡啶溶液中的旋光度会随时间变化，而在空间位阻基2,6-二甲基吡啶中，相同化合物的旋光度保持不变。在两个先前报告的-O-SO2-基团的折射率值中，Tasker和Purves的值得到了确认。单甲基苯基磺酰氯和双甲基苯基磺酰氯是合成L-α-monomesylins和D-α,β-dimesylins的起始物质。

  DOI：

  10.1139/v51-092

文献信息

• Becker, Heinrich; Sharpless, K. Barry, Angewandte Chemie, 1996, vol. 108, # 4, p. 447 - 449
  作者：Becker, Heinrich、Sharpless, K. Barry

  DOI：——

  日期：——
• Synthesis and in Vitro and in Vivo Structure−Activity Relationships of Novel Antifungal Triazoles for Dermatology
  作者：Lieven Meerpoel、Leo J. J. Backx、Louis J. E. Van der Veken、Jan Heeres、David Corens、Alex De Groot、Frank C. Odds、Frans Van Gerven、Filip A. A. Woestenborghs、Andre Van Breda、Michel Oris、Pascal van Dorsselaer、Gustaaf H. M. Willemsens、Karen J. P. Vermuyten、Patrick J. M. G. Marichal、Hugo F. Vanden Bossche、Jannie Ausma、Marcel Borgers

  DOI：10.1021/jm0494772

  日期：2005.3.1

  In search for new compounds with potential for clinical use as antifungal agents in dermatology, a series of 12 azole compounds were synthesized stereospecifically and investigated specifically for their activity against dermatophyte fungal infections in animal models. This panel of azoles was studied in vitro and compared with itraconazole and terbinafine for their antifungal activity using a panel of 24 Candida spp. and 182 dermatophyte isolates. Three azoles (1c, 2c, and 4c) showed in vitro antifungal potency equivalent to itraconazole, but superior to terbinafine, against a panel of 24 Candida spp. with comparable or lower activity than that of itraconazole and terbinafine against 182 dermatophyte isolates and only rare activity against other pathogenic fungi. However, in vivo 1c and 4c, both given orally, demonstrated antifungal activity at least three times greater than itraconazole and were superior compared to terbinafine in M. cants infected guinea pigs. In a mouse model infected by T mentagrophytes, again 4c, but not 1c, showed 5-fold superior activity over itraconazole and terbinafine. Compound 2c was effective in both models but less effective than itraconazole in these models. On the basis of these promising results, 4c is currently being clinically investigated for its potential as a novel antifungal agent against dermatophytosis.
• I. MESYL ESTERS OF GLYCEROL
  作者：Erich Baer、Alan G. Newcombe

  DOI：10.1139/v51-092

  日期：1951.10.1

  The syntheses of L-α-monomesylin, D-α,β- and DL-α,β-dimesylin, and trimesylin are described and some of their physical properties are reported. It was observed that the optical rotations of L-α-monomesylin and D-α,β-dimesylin in pyridine solutions change with time, whereas the rotations of the same compounds in the sterically hindered base, 2,6-lutidine, remain constant. Of the two previously reported values for the refraction of the –O–SO₂– group the value of Tasker and Purves was confirmed. The mono- and dimesylins form the starting materials for the syntheses of the diacyl L-α-monomesylins and the acyl D-α,β-dimesylins.

  本文描述了L-α-monomesylin、D-α,β-dimesylin和DL-α,β-dimesylin、trimesylin的合成方法，并报告了它们的一些物理性质。观察到L-α-monomesylin和D-α,β-dimesylin在吡啶溶液中的旋光度会随时间变化，而在空间位阻基2,6-二甲基吡啶中，相同化合物的旋光度保持不变。在两个先前报告的-O-SO2-基团的折射率值中，Tasker和Purves的值得到了确认。单甲基苯基磺酰氯和双甲基苯基磺酰氯是合成L-α-monomesylins和D-α,β-dimesylins的起始物质。