1、R-C O C R1R-O H+R1C O O HR-O N O2R-O H+H N O3R-O S O3HR-O H+H2S O4R-N H-O O C R1R-N H2+R1C O O HO2OCH3SNHNHOO2OCH3SNHNHOOHRNRCHRNRCOHNHRR+OCH3COSO2NHCONHCH3CSO2NHCONHHOHS-(-)R N O2e-R N O2-e-22H+RN Oe-H+R N OHe-H+RN H O He-22H+R N H2NNO2ONNHOHOAr NN Are-Ar NN Are-H+2ArN HN H Are-2H+2ArN H2+ArN H2(C2
2、H5)2NCSSCSN(C2H5)2(C2H5)2N-C-SHSCH3SOCH3CH3SCH3NCH2CH2CH2N(CH3)2ONCH2CH2CH2N(CH3)2OHOHOOHOOHC OOHOOPOOHOOOH OHNNHOUD PGAROHOATPPPiRAMPOCOASHAMPRCOSCoANH2COOHRCOOHRNHORSHCONHNHCOCOOHNH2COOHC H3S C O AOXC O A S HC H3XON H2-RC H3N H-ROXNNNNNH2HOOHCH3SNH2COOHOH+HX-RCH3-X-R+NNNNNH2HOOHSNH2COOHOHOHOHNHOHN
3、HClClCOOHRHOHRROHHOHHROHROHROHOH2GSHSGOHRXOHRNHNHOONHNHOOOHNNOC4H9ONNOC4H9OOHNHNClClNHOOCSO2N(CH2CH2CH3)2NSRClCH2CH2CH2NMe2R=HR=OHNNCH3OClNNCH3OClOOHOHOHSGOOHOHOHOHNNNHOOHNHNNNHNSHNNNHNSHOHOHNCONH2CYP450NCONH2ONCONH2OHOHRCCHRCCHRCHCORCHCORCH2NCORCOCHRCH2COOHRCH2CONH-PrCH3CH3CH3OHOCH3NHCH3ONCH3CH3CH3
4、NHCH3ONCH3CH3NHCH3ONNNCH3CH3NNHCH3NH2NH2NH2O+NH3OMeNCH3OOHOHNCH3OOHNNNHNSCH3NNNHNSHNHNHOCH3CH3CH3OSNHNHOCH3CH3CH3OONNHCH3SNHNHCH3NCNNNHCH3SNHNHCH3NCNOOOHOPhOOHRCCHR2R3HR1OHCCHR=CH3R1=CH3,R2=OH,R3=HR=C2H5R1=C2H5,R2=H,R3=OHNHNOClRa_R=NO2b_R=NH2ONNHCONH2N2OONNHCONH2NHOH+ONNHCONH2NH2ONHNNHCONH2ONNHCONH2
5、NHNNHSO2NNCOOHOHNNHSO2NH2+COOHOHNH2N2OCHCHOHNHCOCHCl2CH2OHN2OCHCHOHNHCOCOClCH2OHPrOHNHCOCH2OHCHCHN2OCOPrCCl4CYP450Cl4C_.-Cl-Cl3C.H+e-O2CHCl3:CCl3Cl3C-O-O.BrCHClCF3e-Br-HC-CF3.e-H-CF2CClF-F-ClCH=CF2PrPrClCF3HCRHR H2CCF3ClBrCF3ClCHBrCF3ClCOH-Br-CF3COClPrOH2CF3COPrCF3COOHOON+(CH3)3OON+(CH3)3OHN+(CH3)3+
6、COOHCOOHCOOHOACCOOHOH+AcOHNCH3HOOROONH2CXOCH2CH2N(C2H5)2X=NHX=OCH3NHNHCH3ONNHClOCOCH3ONH2COOHOH反应类型反应类型轭合反应式轭合反应式典型药物典型药物O-葡萄糖醛酸苷化葡萄糖醛酸苷化羟基：酚羟基羟基：酚羟基醇羟基醇羟基羧基羧基N葡萄糖醛酸苷化葡萄糖醛酸苷化氨基氨基OHRORGluAcNHOHN2OCHOHCHNHCOCHCl2CH2OHRCRROHRCRROGluPhOOHOR-COOHR-COGluRRNHRRNGluNHCH3酰氨基酰氨基磺酰氨基磺酰氨基S葡萄糖葡萄糖醛酸苷化醛酸苷化硫醇硫醇硫代硫酸
7、硫代硫酸C葡萄糖葡萄糖醛酸苷化醛酸苷化RCONRHRCONRGluCCH3CH3CH2OCH2OCCOONH2NH2RSO2NRHRSO2NRGluNH2SO2NHSNRSHRSGluNNSHCH3SCSHRSCSRGlu(C2H5)2NSSHNNOOPhPhRCOCH2CORRCOCHGluCORNNNNNH2OHOHOPO3H2OPOOSOOHOHO反应类型反应类型轭合反应式轭合反应式典型药物典型药物醇羟基硫醇羟基硫酸酯化酸酯化酚羟基硫酚羟基硫酸酯化酸酯化羟胺硫酸羟胺硫酸酯化酯化氨基的硫氨基的硫酸化酸化RRCHOHRRCHOSO3-RRCH+CH3CH2OHOHROSO3-RCH3CONH
8、OHRRNOHRRNOSO3-RRN+NOC2H5OHORRN HRRN SO3-RRCH+OHNHOHOHOHNHCOCH3NN(CH3)2BrNNH2BrNCHOBrNCOOHBrNNHCOOHOBr反应类型反应类型轭合反应式及典型药物反应式轭合反应式及典型药物反应式1.亲核取代反应亲核取代反应（SN2）例子：例子：RXYGSHRXSGX=CH2.O,S Y=C H3O2S OO O S O2C H3-S G:S GO S O2H3CS+GHONO2ONO2ONO2GS-HONO2ONO2OSG-SGHONO2ONO2OH+GSSGOGS-HSGHH2.芳环芳环亲核取亲核取代反应代反应例子
9、：例子：3.酰化酰化反应反应例子：例子：XSGGSHzzNNNNNO2SCH3NHNNNNNNO2SCH3NHNSG-SGNNNO2SGCH3+NNSHNHNRClOCHS GRS GOCRNCXGSHRNCSGXCHCl3ClCClOGSHGSCOSGCH3-N=C=OGSHCH3NHCSGO4、Michael加成反应加成反应例子：例子：5.还原反应还原反应RRCHCXRRCRSGCH2XX=COR.CNOOHNCH3OHHOOHNCH3OSGOOHNCH3OSGOXOHxHNORNHSORG反应类型反应类型轭合反应式轭合反应式典型药物典型药物脂肪胺轭合脂肪胺轭合反应反应芳香族轭合芳香族轭合
10、反应反应肼和酰肼轭肼和酰肼轭合反应合反应RRNHRRNCOCH5CH3CH3HNHOSCOOHNH2HCOOHRN H2RN HCOCH3R NHNH2R NHNHCOCH3HOOCOHNH2NCONHNH2NNNHNH2OOHOPO3H2NNNNNH2OPOOHOPOOHCH2OCCH3CH3NHCOCHCH2CH2CONHCH2CH2-S-COCH3OH反应类型反应类型轭合反应式轭合反应式典型药物典型药物酚羟基甲基化酚羟基甲基化反应反应氨基甲基化反氨基甲基化反应应杂环氮原子甲杂环氮原子甲基化反应基化反应吡啶氮原子甲吡啶氮原子甲基化反应基化反应巯基的甲基化巯基的甲基化反应反应OHOHROHO
11、MeROHOHOHNHRNRHRNRCH3OOOHNH2NHNH-CH3NNNNHOOCH3CH3NRN+RCH3NCONH2COOHNCH3SHHORSHRSCH3OHOHCHR2CH2NHR1R1=H,R2=HR1=H,R2=OHR1=CH3,R2=OHCH2CH2CH2CH2CH2N(CH3)3CH2CH2CH2CH2CH2N(CH3)3+.Br2CH2COOCH2CH2N(CH3)3CH2COOCH2CH2N(CH3)3+CH3CH3NHCOCH2NC2H5C2H5CH3CH3NHCOCHNH2CH3CHNH2ONSCOORCONHR=HR=CH2OCC(CH3)3OOCOCH3OOOCOCH3OOCH3NC2H5OHCH3
