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Synthesis of novel 15-membered macrolide derivatives 被引量:2

Synthesis of novel 15-membered macrolide derivatives
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摘要 In order to develop new antibiotics effective against resistant bacteria,a series of novel 15-membered macrolide derivatives were designed and synthesized by the modification of hydroxyl groups at C-11,C-12 and C-4" positions.Their structures were confirmed by MS,IR,^1H NMR or ^13C NMR. In order to develop new antibiotics effective against resistant bacteria,a series of novel 15-membered macrolide derivatives were designed and synthesized by the modification of hydroxyl groups at C-11,C-12 and C-4" positions.Their structures were confirmed by MS,IR,^1H NMR or ^13C NMR.
机构地区 School of Pharmacy
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2008年第4期409-411,共3页 中国化学快报(英文版)
基金 supported by NNSFC(No.20372043),Shandong Science and Technology Promotion Project(No.2005GG3202098) Natural Science Foundation of Shandong Province(No.Y2006C31).
关键词 MACROLIDE Azithromycin derivatives SYNTHESIS 4"-Carbamate derivatives Macrolide Azithromycin derivatives Synthesis 4"-Carbamate derivatives
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  • 9[9]Spectral data of representational compounds:4a:white crystals,IR (KBr):3475,2972,2937,2877,2830,2788,1727,1632,1507,1457,1378,1344,1255,1170,1109,1094,1073,1050,1036,1014 cm-1,1H NMR (600 MHz,CDCl3,δ ppm):7.36 (m,1H,HAr),7.23-7.18 (m,3H,HAr),5.15 (d,1H,CH),4.71 (d,1 H,1"-CH),4.59 (t,1H,13-CH),4.54-4.90 (m,2H,4"-CH,5"-CH),4.51 (m,2H,CH2CH2Ar),4.27 (m,1H,2'-CH),3.70-3.64 (m,3H,5'-CH,3-CH and 11-CH),3.59-3.46 (m,2H.CH2CH2Ar) 3.31 (s,3H,3"-OCH3),2.87 (m,1H,10-CH),2.79 (m,1H,3'-CH),2.71(m,1H,2-CH),2.54 (d,1H,5-CH),2.40 (m,3H,9a-NCH3),2.33 (s,6H,3"-N(CH3)2),2.18 (s,1H,9b-CH),2.07 (m,1H,4-CH),2.00 (m,2H,9a-CH and 2"b-CH),1.90 (m,2H,8-CH),1.79 (d,1H,2"a-CH),1.65 (dd,1H,4'b-CH),1.64 (dd,1H,4'a-CH),1.48 (m,1H,7b-CH),1.31 (s,3H,6-CH3),1.28 (m,1H,7a-CH),1.21 (m,2H,13-CH2CH3),1.20-1.19 (m,6H,2-CH3 and 5"-CH3),1.15 (s,3H,3"-CH3),1.11-1.09 (m,9H,5'-CH3,10-CH3 and 12-CH3),1.06 (d,3H,8-CH3),0.92-0.89 (m,6H,4-CH3 and 13-CH2CH3),12C NMR (600 MHz,CDCl3,δ ppm):178.7 (C-1),156.3 (CONHCH2CH2Ar),136.2 (C-1''',Ar),134.1 (C-2''',Ar),131.1 (C-3''' At),129.6 (C-6''',Ar),128.1 (C-4''',Ar),126.9 (C-5''',Ar),102.4 (C-1'),95.0 (C-1"),83.1 (C-5),79.3 (C-13),77.2 (C-3 and C-3"),77.0 (C-12 and C-2'),76.8 (C-6 and C-11),74.3 (C-9),74.0 (C-3"),73.5 (C-5'),73.1 (C-3'),71.0 (C-5"),68.7 (C-10),65.4 (3"-OCH3),63.2 (C-2),49.4 (C-7),45.0 (3'-N(CH3)2),42.4 (C-4),41.6 (10-NCH3),40.6 (CH2CH2Ar),36.4 (C-2"),35.1 (C-4'),33.8 (C-8),27.4 (CH2CH2Ar),26.8 (5'-CH3),21.9 (6-CH3),21.6 (3'-CH3),21.2 (13-CH2CH3),21.1 (8-CH3),17.8 (12-CH3),16.2 (5"-CH3),14.9 (10-CH3),11.3 (2-CH3),9.3 (4-CH3),7.5 (13-CH2CH3);MS:m/z calcd,for C47H80ClN3O13 930.6;found (M+1)+ 931.6.7a:white crystals,IR (KBr):3427,2973,2937,2880,2830,1813,1727,1605,1510,1456,1381,1353,1337,1223,1111,1093,1073,1046,1015 cm-1,1H NMR (600 MHz,CDCl3,δ ppm):7.25 (m,2H,HAr),7.02 (m,2H,HAr),5.20 (d,1H,1'-CH),5.09 (d,1H,1"-CH),4.90 (m,1H,13-CH),4.61 (d,1H,11-CH),4.47 (t,1H,4"-CH,),4.43-4.33 (m,6H,5"-CH,2'-CH,CH2Ar,5'-CH and 3-CH),3.64 (m,1H,10-CH),3.61 (d,1H,5-CH),3.32 (s,3H,3"-OCH3),2.86 (m,2H,2-CH and 3'-CH),2.41 (m,6H,3"-N(CH3)2),2.36 (d,1H,9b-CH),2.21 (s,3H,9a-NCH3),2.18 (m,1H,4-CH),2.05 (m,2H,9a-CH and 2"b-CH),1.95 (m,1H,8-CH),1.93 (m,1H,2"a-CH),1.83 (m,2H,4'b-CH and 7a-CH),1.64 (m,2H,7b-CH and 4'a-CH),1.60 (m,2H,13-CH2CH3),1.45 (s,3H,12-CH3),1.29 (s,3H,3"-CH3),1.22 (d,6H,2-CH3 and 6-CH3),1.18 (m,6H,5'-CH3 and 5"-CH3),1.07 (m,6H,10-CH3 and 8-CH3),0.93 (m,6H,4-CH3 and 13-CH2CH3);MS:m/z calcd,for C47H76FN3O14 926.1;found (M+1)+ 927.1.

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