5-butyramido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid | 24967-29-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-butyramido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid
• 英文别名: (2R,3R,4S)-3-(butanoylamino)-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 24967-29-1
• 化学式: C₁₃H₂₁NO₈
• 分子量: 319.312
• InChiKey: QMDABYTUXUBWJL-MXMUJRTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2,6-anhydro-3,5-dideoxy-5-trifluoroacetamido-D-glycero-D-galactonon-2-enonate 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 5-butyramido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid
  参考文献：
  名称：

  Synthesis and chemical characterization of several perfluorinated sialic acid glycals and evaluation of their in vitro antiviral activity against Newcastle disease virus

  摘要：

  一些C-5修饰的唾液酸糖醛的合成和生物评价，C-4位置是否发生了表异构化，作为新城疫病毒(HN)抑制剂的评估。

  DOI：

  10.1039/c7md00072c

文献信息

• Selective Inhibitors of Human Neuraminidase 1 (NEU1)
  作者：Tianlin Guo、Rachel Héon-Roberts、Chunxia Zou、Ruixiang Zheng、Alexey V. Pshezhetsky、Christopher W. Cairo

  DOI：10.1021/acs.jmedchem.8b01411

  日期：2018.12.27

  Inhibitors of human neuraminidase enzymes (NEU) are recognized as important tools for the study of the biological functions of NEU and will be potent tools for elucidating the role of these enzymes in regulating the repertoire of cellular glycans. Here we report the discovery of selective inhibitors of the human neuraminidase 1 (NEU1) and neuraminidase 2 (NEU2) enzymes with exceptional potency. A library

  人神经氨酸酶（NEU）的抑制剂被认为是研究NEU生物学功能的重要工具，将是阐明这些酶在调节细胞聚糖组成中的作用的有效工具。在这里，我们报告发现人类神经氨酸酶1（NEU1）和神经氨酸酶2（NEU2）酶具有特殊效力的选择性抑制剂的发现。修饰的2-deoxy-2,3-didehydro- N的文库合成了具有乙酰基神经氨酸（DANA）类似物的C5-或C9位置，并针对四种人类神经氨酸酶同工酶（NEU1-4）进行了评估。NEU1可以很好地容纳在C5和C9位置带有酰胺连接基的疏水基团，并且发现一个六氨基基团在两个位置均具有最佳效价。尽管C5-六氨基-C9-六氨基-DANA类似物未显示出协同修饰的协同改进，但在单个位置上延伸的烷基酰胺与第二个位置上的较小基团相结合，增强了效力。确定的最佳NEU1抑制剂是具有K i与其他同工酶相比，具有53±5 nM的选择性和340倍的选择性。此外，我们证明了C5修饰结合C
• Compounds useful for inhibiting paramyxovirus neuraminidase
  申请人：——

  公开号：US20030187063A1

  公开（公告）日：2003-10-02

  Compounds represented by the formula: 1 wherein X is selected from the group consisting of: CHR, O, NR, N—OR, NR(O), S, S(O) and S(O)O X 1 is selected from the group consisting of CR, N, and N(O); R is selected from the group consisting of: H, alkyl, alkene, alkyne, CN, NO 2 , N 3 , halo and NHR 10 ; R 1 is selected from the group consisting of: H, (CH 2 )nCO 2 R 10 , (CH 2 )n-tetrazol, (CH 2 )nSO 3 H, (CH 2 )nSO 2 H, (CH 2 )nPO 3 H 2 , (CH 2 )nCONR 10 , (CH 2 )nNO 2 , and (CH 2 )nCHO; R 1a is selected from the group consisting of: H, (CH 2 )nOR 10 , (CH 2 )nCN, (CH 2 )nNR 10 R 10a , (CH 2 )nNHC(O)R 10 , (CH 2 )nC(O)NR 10 R 10a , and (CH 2 )nOC(O)R 10 ; R 1 and R 1a both cannot be H each of R 2 and R 2a is independently selected from the group consisting of H, halo, CN, (CH 2 )nCO 2 R 10 , (CH 2 )nNR 10 R 10a and (CH 2 ) n —OR 10 ; each of R 3 and R 3a is independently selected from the group consisting of: H, NHSO 2 R 10 , N(O)—SO 2 R 10 , NR 10 SO 2 R 10a , (CH 2 )mYR 10 , and (CH 2 )mR 6 ; at least one of R 3 and R 3a should be other than H Y is selected from the group consisting of: O, NH, NHC(O), C(O)NH, S, S(O), S(O)O, NHS(O)O, S(O)ONH, NHC(O)NH and heterocycle; R 3 and R 3a together may be ═O, ═CHR 6 , ═CHR 10 , ═NR 10 , NR 10 and ═N—OR 10 R 4 and R 4a is independently selected from the group consisting of: H, (CH 2 )mYR 10 and (CH 2 )mR 6 R 4 and R 4a together may be: ═O, ═CHR 6 , ═CHR 10 , ═NR 10 and ═N—OR 10 each of R 5 and R 5a is independently selected from the group consisting of C(R 7 )(R 7a ), C(R 7 )(R 7a )C(R 8 )(R 8a ), C(R 7 )(R 7a )C(R 8 )(R 8a )C(R 9 )(R 9a ), OC(R 7 )(R 7a ), OC(R 7 )(R 7a )C(R 8 )(R 8a ), C(R 7 )(R 7a )OC(R 8 )(R 8a ), N(R 10 )C(R 7 )(R 7a ), N(R 10 ) C(R 7 )(R 7a )C(R 8 )(R 8a ), C(R 7 )(R 7a )N(R 10 )C(R 8 )(R 8a ), and C(O)NR 10 R 10a ; R 6 is selected from the group consisting of H, halo, CN, NO 2 , N 3 , CO 2 R 10 , R 10 and NR 10 R 10a ; R 7 , R 7a , R 8 , R 8a , R 9 and R 9a is selected from the group from the group consisting of: H, (CH 2 )mYR 10 and (CH 2 )mR 6 each of the R 10 and R 10a is individually selected from the groups consisting of: H, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, alkenyl, substituted alkenyl, alkynyl, and substituted alkynyl; Each of m and n is individually 0, 1, 2, 3, or 4; and pharmaceutically acceptable salt thereof; and prodrugs thereof, and uses thereof.

  该化合物的结构式为：1，其中X从以下组中选择：CHR，O，NR，N—OR，NR（O），S，S（O）和S（O）OX1从以下组中选择：CR，N和N（O）；R从以下组中选择：H，烷基，烯烃，炔烃，CN，NO2，N3，卤素和NHR10；R1从以下组中选择：H，（CH2）nCO2R10，（CH2）n-四唑，（CH2）nSO3H，（CH2）nSO2H，（CH2）nPO3H2，（CH2）nCONR10，（CH2）nNO2和（CH2）nCHO；R1a从以下组中选择：H，（CH2）nOR10，（CH2）nCN，（CH2）nNR10R10a，（CH2）nNHC（O）R10，（CH2）nC（O）NR10R10a和（CH2）nOC（O）R10；R1和R1a都不能是H；R2和R2a各自从H，卤素，CN，（CH2）nCO2R10，（CH2）nNR10R10a和（CH2）n—OR10中选择；R3和R3a各自从H，NHSO2R10，N（O）—SO2R10，NR10SO2R10a，（CH2）mYR10和（CH2）mR6中选择；其中至少有一个R3和R3a不是H，Y从以下组中选择：O，NH，NHC（O），C（O）NH，S，S（O），S（O）O，NHS（O）O，S（O）ONH，NHC（O）NH和杂环；R3和R3a可以组成&boxH；O，&boxH；CHR6，&boxH；CHR10，&boxH；NR10，NR10和&boxH；N—OR10；R4和R4a各自从H，（CH2）mYR10和（CH2）mR6中选择；其中R5和R5a各自从C（R7）（R7a），C（R7）（R7a）C（R8）（R8a），C（R7）（R7a）C（R8）（R8a）C（R9）（R9a），OC（R7）（R7a），OC（R7）（R7a）C（R8）（R8a），C（R7）（R7a）OC（R8）（R8a），N（R10）C（R7）（R7a），N（R10）C（R7）（R7a）C（R8）（R8a），C（R7）（R7a）N（R10）C（R8）（R8a）和C（O）NR10R10a中选择；R6从以下组中选择：H，卤素，CN，NO2，N3，CO2R10，R10和NR10R10a；R7、R7a、R8、R8a、R9和R9a从以下组中选择：H，（CH2）mYR10和（CH2）mR6；R10和R10a各自从以下组中选择：H，烷基，取代烷基，芳基，取代芳基，芳基烷基，取代芳基烷基，杂环，取代杂环，烯基，取代烯基，炔基和取代炔基；m和n各自为0、1、2、3或4；以及其药学上可接受的盐和前药，以及其用途。
• US7045535B2
  申请人：——

  公开号：US7045535B2

  公开（公告）日：2006-05-16
• Synthesis and chemical characterization of several perfluorinated sialic acid glycals and evaluation of their in vitro antiviral activity against Newcastle disease virus
  作者：P. Rota、N. Papini、P. La Rocca、M. Montefiori、F. Cirillo、M. Piccoli、R. Scurati、L. Olsen、P. Allevi、L. Anastasia

  DOI：10.1039/c7md00072c

  日期：——

  Synthesis and biological evaluation of some C-5 modified sialic acid glycals, epimerized or not at the C-4 position, as HN inhibitors of Newcastle Disease Virus (NDV).

  一些C-5修饰的唾液酸糖醛的合成和生物评价，C-4位置是否发生了表异构化，作为新城疫病毒(HN)抑制剂的评估。