(2R,3R,4S)-3-(Acetylamino)-4-azido-2-[(isobutylamino)carbonyl]-3,4-dihydro-2H-pyran-6-carboxylic acid | 464180-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3R,4S)-3-(Acetylamino)-4-azido-2-[(isobutylamino)carbonyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• 英文别名: (2R,3R,4S)-3-acetamido-4-azido-2-(2-methylpropylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 464180-43-6
• 化学式: C₁₃H₁₉N₅O₅
• 分子量: 325.324
• InChiKey: MIJLWEGZVNYSGF-JMJZKYOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

文献信息

• 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。
• [EN] COMPOUNDS USEFUL FOR INHIBITING PARAMYXOVIRUS NEURAMINIDASE<br/>[FR] COMPOSES D'INHIBITION DE LA NEURAMINIDASE DE PARAMYXOVIRUS
  申请人：BIOCRYST PHARM INC

  公开号：WO2002076971A1

  公开（公告）日：2002-10-03

  Compounds represented by the formulae (A, B, C) wherein X is selected from the group consisting of: CHR, O, NR, N-OR, NR(O), S, S(O) and S(O)O X1 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, NO2, N3, halo and NHR10; R1 is selected from the group consisting of: H, (CH2)nCO2R10, (CH2)n-tetrazol, (CH2)nSO3H, (CH2)nSO2H, (CH2)nPO3H2, (CH2)nCONR10, (CH2)nNO2, and (CH2)nCHO; R1a is selected from the group consisting of: H, (CH2)nOR10, (CH2)nCN, (CH2)nNR10R10a, (CH2)nNHC(O)R10, (CH2)nC(O)NR10R10a, and (CH2)nOC(O)R10; R1 and R1a both cannot be H each of R2 and R2a is independently selected from the group consisting of H, halo, CN, (CH2)nCO2R10, (CH2)nNR10R10a and (CH2)n-OR10; each of R3 and R3a is independently selected from the group consisting of: H, NHSO2R10, N(O)-SO2R10, NR10SO2R10a, (CH2)mYR10, and (CH2)mR6; at least one of R3 and R3a 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; R3 and R3a together may be =O, =CHR6, =CHR10, NR10 and =N-OR10 R4 and R4a is independently selected from the group consisting of: H, (CH2)mYR10 and (CH2)mYR10 and (CH2)mR6 R4 and R4a together may be: =O, =CHR6, =CHR10, =NR10 and =N-OR10 each of R5 and R5a is independently selected from the group consisting of 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)(R¿7a)OC(R8)(R8a), N(R10)C(R7)(R7a), N(R10)C(R7)(R7a)C(R8)(R8a), C(R7)(R7a)N(R10)C(R8a), and C(O)NR10R10a; R6 is selected from the group consisting of H, halo, CN, NO2, N3, CO2R¿10, R¿10? and NR10R10a; R7, R7a, R8, R8a, R9 and R9a is selected from the group from the group consisting of: H, (CH2)mYR10 and (CH2)mR6 each of the R10 and R10a 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 O, 1, 2, 3, or 4; and pharmaceutically acceptable salt thereof; and prodrugs thereof, and uses thereof.

  由公式（A，B，C）表示的化合物，其中X选择自以下组：CHR，O，NR，N-OR，NR（O），S，S（O）和S（O）O X1选择自以下组：CR，N和N（O）; R选择自以下组：H，烷基，烯烃，炔烃，CN，NO2，N3，卤素和NHR10; R1选择自以下组：H，（CH2）nCO2R10，（CH2）n-四唑，（CH2）nSO3H，（CH2）nSO2H，（CH2）nPO3H2，（CH2）nCONR10，（CH2）nNO2和（CH2）nCHO; R1a选择自以下组：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中的每一个都独立地选择自以下组：H，卤素，CN，（CH2）nCO2R10，（CH2）nNR10R10a和（CH2）n-OR10; R3和R3a中的每一个都独立地选择自以下组：H，NHSO2R10，N（O）-SO2R10，NR10SO2R10a，（CH2）mYR10和（CH2）mR6; R3和R3a中至少有一个应该不是H，Y选择自以下组：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在一起可以是=O，=CHR6，=CHR10，NR10和=N-OR10 R4和R4a独立地选择自以下组：H，（CH2）mYR10和（CH2）mYR10和（CH2）mR6; R4和R4a在一起可以是：=O，=CHR6，=CHR10，=NR10和=N-OR10，R5和R5a中的每一个都独立地选择自以下组：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）（R¿7a）OC（R8）（R8a），N（R10）C（R7）（R7a），N（R10）C（R7）（R7a）C（R8）（R8a），C（R7）（R7a）N（R10）C（R8a）和C（O）NR10R10a; R6选择自以下组：H，卤素，CN，NO2，N3，CO2R¿10，R¿10？和NR10R10a; R7，R7a，R8，R8a，R9和R9a选择自以下组：H，（CH2）mYR10和（CH2）mR6，R10和R10a中的每一个都单独选择自以下组：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，烯烃，取代烯烃，炔烃和取代炔烃; m和n中的每一个都是O、1、2、3或4;及其医药上可接受的盐;及其前药和用途。
• US7045535B2
  申请人：——

  公开号：US7045535B2

  公开（公告）日：2006-05-16