(S)-4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl trifluoromethanesulfonate | 301220-98-4

• 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: (S)-4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl trifluoromethanesulfonate
• 英文别名: [(3S)-4,4-dimethyl-2-oxooxolan-3-yl] trifluoromethanesulfonate
• CAS: 301220-98-4
• 化学式: C₇H₉F₃O₅S
• 分子量: 262.207
• InChiKey: XMEVZEMJXYDCFH-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl trifluoromethanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以35%的产率得到(R)-3-azido-4,4-dimethyl-tetrahydrofuran-2-one
  参考文献：
  名称：

  Structure–activity relationships and enzyme inhibition of pantothenamide-type pantothenate kinase inhibitors

  摘要：

  A set of novel pantothenamide-type analogues of the known Staphylococcus aureus pantothenate kinase (SaPanK) inhibitors, N-pentyl, and N-heptylpantothenamide, was synthesized in three series. The first series of analogues (1-3) were designed as molecular probes of the PanK binding site to elucidate important structure-activity relationships (SAR). The second series of analogues (4-16) were designed using Structural information obtained from the Escherichia coli PanK (EcPanK) Structure by targeting the pantothenate binding site and the adjacent phenylalanine-lined lipophilic pocket. Insight into the antimicrobial effect of N-pen- tylpantothenamide (N5-Pan) through its Conversion to the antimetabolite ethyldethia-CoA and further incorporation into all inactive acyl carrier protein analogue drove the development of the third series of analogues (17-25) to enhance this effect using substrate-like substitutions. Each of the analogues was screened for enzyme inhibition activity against a panel of pantothenate kinases consisting of EcPanK, Aspergillus nidulans (AnPanK), SaPanK, and the murine isoform (MmPanK1 alpha). Series 1 demonstrated only modest inhibitory activity, but did reveal some important SAR findings including stereospecific binding. Series 2 demonstrated a much higher inhibition rate for the entire series and significant inhibition was seen with analogues containing alkyl substituents. Series 3 demonstrated the most preferential inhibition profile, with the highest inhibitory activity against the SaPanK greater selectivity. The overall activity data from these analogues Suggest a complex and non-enzynie specific SAR for pantotheriamide substrate/inhibitors of the different PanK enzymes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.021
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (S)-(+)-泛解酸内酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以91%的产率得到(S)-4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Structure–activity relationships and enzyme inhibition of pantothenamide-type pantothenate kinase inhibitors

  摘要：

  A set of novel pantothenamide-type analogues of the known Staphylococcus aureus pantothenate kinase (SaPanK) inhibitors, N-pentyl, and N-heptylpantothenamide, was synthesized in three series. The first series of analogues (1-3) were designed as molecular probes of the PanK binding site to elucidate important structure-activity relationships (SAR). The second series of analogues (4-16) were designed using Structural information obtained from the Escherichia coli PanK (EcPanK) Structure by targeting the pantothenate binding site and the adjacent phenylalanine-lined lipophilic pocket. Insight into the antimicrobial effect of N-pen- tylpantothenamide (N5-Pan) through its Conversion to the antimetabolite ethyldethia-CoA and further incorporation into all inactive acyl carrier protein analogue drove the development of the third series of analogues (17-25) to enhance this effect using substrate-like substitutions. Each of the analogues was screened for enzyme inhibition activity against a panel of pantothenate kinases consisting of EcPanK, Aspergillus nidulans (AnPanK), SaPanK, and the murine isoform (MmPanK1 alpha). Series 1 demonstrated only modest inhibitory activity, but did reveal some important SAR findings including stereospecific binding. Series 2 demonstrated a much higher inhibition rate for the entire series and significant inhibition was seen with analogues containing alkyl substituents. Series 3 demonstrated the most preferential inhibition profile, with the highest inhibitory activity against the SaPanK greater selectivity. The overall activity data from these analogues Suggest a complex and non-enzynie specific SAR for pantotheriamide substrate/inhibitors of the different PanK enzymes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.021

文献信息

• [EN] PYRROLIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] PYRROLIDINES MODULATEURS DE L'ACTIVITE DU RECEPTEUR DE CHIMIOKINE
  申请人：MERCK & CO INC

  公开号：WO2000059502A1

  公开（公告）日：2000-10-12

  The present invention is directed to pyrrolidine compounds of formula (I) (wherein R?1, R2, R3, R4, R5, R6, R14¿ and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式(I)的吡咯烷化合物（其中R1，R2，R3，R4，R5，R6，R14和n在此定义），其作为趋化因子受体活性调节剂具有用途。特别地，这些化合物作为趋化因子受体CCR-5和/或CCR-3的调节剂具有用途。
• EP1171122A4
  申请人：——

  公开号：EP1171122A4

  公开（公告）日：2002-05-29
• PYRROLIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Merck & Co., Inc.

  公开号：EP1171122A1

  公开（公告）日：2002-01-16
• US6248755B1
  申请人：——

  公开号：US6248755B1

  公开（公告）日：2001-06-19