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Synthesis of a new series of anti-rhinovirus compounds

Synthesis of a new series of anti-rhinovirus compounds
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摘要 The synthesis of a series of 3,6-dichloropyridazine derivatives was described. In vitro experiment, all compounds exhibited an anti-rhinovirus activity, and one of the compounds 6g showed the comparable activity as our lead compound pirodavir. The synthesis of a series of 3,6-dichloropyridazine derivatives was described. In vitro experiment, all compounds exhibited an anti-rhinovirus activity, and one of the compounds 6g showed the comparable activity as our lead compound pirodavir.
作者 Shi Yong Fan Chun Lai Mi Jun Yang Song Li Zhi Bing Zheng
机构地区 Institute of Pharmacology and Toxicology School of Pharmaceutical Engineering
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第4期400-402,共3页 中国化学快报（英文版）
基金 the National Basic Research Program of China （No. 2004CB 518908） the National Natural Science Foundation of China （No. 30472092）.
关键词 3 6-Dichoropyridazine derivatives SYNTHESIS Anti-rhinovirus 3,6-Dichoropyridazine derivatives Synthesis Anti-rhinovirus
分类号 O626.4 [理学—有机化学] R914.5 [医药卫生—药物化学]
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参考文献8

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  • 8[8]6a:1H NMR (400 MHz,CDCl3,δ ppm,J Hz):7.26-7.24 (m,2H),6.93-6.91 (m,2H),6.86 (s,1H),4.16-4.13 (t,2H,J = 5.3 Hz),3.70 (s,2H),3.38-3.36 (t,4H,J = 4.8 Hz),2.92-2.89 (t,2H,J = 5.3 Hz),2.81-2.78 (t,4H,J = 4.8 Hz); EI-MS (m/z,%):395.0[M+ + 4,1.3],393.0[M+ + 2,8.4],391.0[M+,12.0],259.0[2.0],249.0[23.0],247.0[100.0],245.0[94.0],175.1[24.0]; m.p.(℃):137-139; Eluent agent (by volume):petroleum:ethyl ether:methanol = 4:4:0.1.6b:1H NMR (400 MHz,CDCl3,δ ppm,JHz):8.22-8.20 (d,2H,J = 9 Hz),7.40 (s,1H),7.20-7.17 (d,2H,J= 9 Hz),4.30-4.27 (t,2H,J= 5.6 Hz),3.35-3.33 (m,4H),2.83-2.81 (t,2H,J= 5.6 Hz),2.68-2.66 (m,4H); EI-MS (m/z,%):399.0[M+ + 2,2.6],397.0[M+,4.0],249.0[12.0],247.0[63.0],245.0[100.0],175.0[7.0]; m.p.(℃):128-129; Eluent agent (by volume):petroleum:ethyl ether:methanol = 1:0.5:0.1.6c:1H NMR (400 MHz,CDCl3,δ ppm,J Hz):7.84-7.82 (m,1H),7.55-7.54 (m,1H),7.11-7.08 (m,2H),6.87 (s,1H),4.30-4.28 (t,2H,J= 5.3 Hz),3.37-3.35 (m,4H),2.97-2.95 (t,2H,J= 5.3 Hz),2.87-2.85 (m,4H); EI-MS (m/z,%):396.9[M+,1.2],379.9[1.2],258.9[7.3],248.9[16.0],246.9[80.0],244.9[100.0],229.9[6.2],175.0[12.0]; m.p.(℃):125-126; Eluent agent (by volume):petroleum:ethyl ether:methanol = 8:6:0.3.6d:1H NMR (400 MHz,CDCl3,δ ppm,J Hz):8.75-8.74 (d,1H,J = 2.2 Hz),8.18-8.15 (m,1H),7.38 (s,1H),6.96-6.94 (d,1H,J = 8.7 Hz),4.51-4.48 (t,2H,J = 5.6 Hz),3.85 (s,3H),3.34-3.33 (m,4H),2.80-2.87 (t,2H,J = 5.6 Hz),2.66-2.65 (m,4H); EI-MS (m/z,%):411.1[M+,2.0],376.1[3.2],262.1[14.3],260.1[61.0],258.1[92.0],249.1[12.0],247.1[61.0],245.1[100.0],223.1[90.0],180.1[42.0]; m.p.(℃):145-146; Eluent agent (by volume):petroleum:ethyl ether:methanol = 10:5:0.2.6e:1H NMR(400 MHz,CDCl3,δppm,J Hz):7.03-7.01 (d,2H,J = 7.3 Hz),6.95-6.91 (m,1H),6.89 (s,1H),3.94(brs,2H),3.41 (brs,4H,),2.90 (brs,2H),2.83 (brs,4H),2.29 (s,6H); EI-MS (m/z,%):382.0[M+ + 2,4.6],380.0[M+,6.3],260.9[8.6],258.9[12.0],249.0[21.0],247.0[100],245.0[87.0],175.0[15.0]; m.p.(℃):94-96; Eluent agent (by volume):petroleum:acetone = 6:1.6f:1H NMR (400 MHz,CDCl3,δ ppm,J Hz):7.32-7.30 (dd,2H,J1 = 6.4 HZ,J2 = 2.0 Hz),6.86 (s,1H),6.87-6.85 (dd,2H,J1 = 5.6 Hz,J2 = 2.4 Hz),4.15-4.12 (t,2H,J = 5.6 Hz),3.37-3.35 (m,4H),2.91-2.88 (t,2H,J =.5.6 Hz),2.80-2.78 (m,4H),1.30 (s,9H); EI-MS (m/z,%):412.0[M+ + 4,1.6],410.0[M+ + 2,6.4],408[M+,8.7],248.9[24.0],246.9[77.0],244.9[100.0],175.0[21.0]; m.p.(℃):97-99; Eluent agent (by volume):petroleum:acetone=5:1.6g:1H NMR(400 MHz,CDCl3,δ ppm,J Hz):6.92-6.85 (m,5H),4.28 (m,2H),4.01-3.96 (q,2H,J = 7 Hz),3.53 (brs,4H),3.07 (brs,6H),1.42-1.38 (t,3H,J = 7 Hz); EI-MS (m/z,%):400.1[M+ + 4,1.2],398.1[M+ + 2,8.1],396.1[M+,10.9],263.0[6.0],261.0[32.0],259.0[52.0],249.0[12.0],247.0[75.6],245.0[100.0],230.0[6.0],175.1[15.0]; m.p.(℃):93-95; Eluent agent (by volume):petroleum:ethyl ether:methanol = 10:3:0.5.
Chinese Chemical Letters
2007年 第4期

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