脱氢枞胺Schiff碱及其配合物的合成与表征
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摘要
脱氢枞胺是一种具有光学活性的胺，它可由脱氢枞酸经胺化生成松香腈后氢化而得。它是一种重要的林产品，在造纸、医药、农药、化工等方面有着广泛的应用。由于它是松香酸的衍生物，因而脱氢枞胺及其醋酸盐具有一定的生物活性，可以作为优异的杀虫剂、杀菌剂和杀藻剂；另外，由于脱氢枞胺中存在天然手性碳，因而它可以作为优良的光学拆分剂。Schiff碱及其配合物由于具有生物活性及不对称催化的活性，因而也是目前研究的热点之一。
本论文研究了目前未见国内外文献报道的、水杨醛中苯环上含有取代基的水杨醛缩脱氢枞胺Schiff碱及其金属配合物的合成与表征，共计获得了21个新的化合物，从而为后期生物活性的测定及不对称催化提供研究基础和实验样品。
在Schiff碱的合成中，我们以无水乙醇为溶剂，利用醛与氨基能够发生氨解反应的性质，在加热条件下，将系列取代水杨醛(水杨醛、5-氯水杨醛、5-硝基水杨醛、5-溴水杨醛、3，5-二氯水杨醛、3，5-二溴水杨醛、4-羟基水杨醛、4-二乙氨基水杨醛、4-甲氧基水杨醛)的乙醇溶液滴加到脱氢枞胺-乙醇溶液中，经缩合得到9个Schiff碱，其中8个Schiff碱未见文献报道。通过IR、UV、~1HNMR、MS及元素分析等手段，对新Schiff碱进行了表征。
利用Schiff碱能够与金属离子配位的性质，我们选取了Mn~(2+)、Co~(2+)、Fe~(3+)、Cu~(2+)和Ni~(2+)离子与系列Schiff碱进行配位。反应以无水乙醇为溶剂，在N_2氛围下，分别将Mn~(2+)、Co~(2+)、Fe~(3+)、Cu~(2+)和Ni~(2+)的乙醇溶液缓慢滴加到热的Schiff碱-KOH溶液中。反应最终得到了8个铜系Schiff碱配合物和6个镍系配合物。其中镍系配合物和7个铜系配合物未见文献报道。用IR、UV、MS及元素分析等手段对配合物进行了表征，结果表明亚胺基上的N原子及酚羟基上的氧原子参与了金属离子的配位，形成了N，N，O，O四配位的铜、镍配合物。
Dehydroabietylamine is a kind of optical active amine, which derived from dehydroabietic acid. Thus dehydroabietylamine and its acetates have showed some bioactivities such as pesticide, bactericide and algaecide. It is a sort of important forestry product, which can be applied in papermaking, medicine, pesticide, chemical industries etc. It can also be used as chiral resolution agent. With the properties of bioactivities and asymmetric catalytic activities, the research of Schiff bases and their complexes is also one of the active fields.
Our main research work has been focused on the synthesis, characterization of substituted salicylaldehyde Schiff bases and their complexes, which are not reported in articles now. There are twenty-one new compounds in total.
Nine Schiff bases were prepared by condensation of amine with substituted salicylaldehydes. To a solution of chiral amine (dehydroabietylamine) in dry ethanol, substituted salicylaldehyde-ethanol solution was added and the mixture was refluxed for 3h, then filtrated or evaporated the solvent. Some Schiff bases were purified by recrystallized. In this section, eight compounds are not reported in articles. Some new Schiff bases were characterized by IR, UV,1HNMR and elemental analyses.
These Schiff bases are normally bidentate ligands, which can provide O and N atoms to coordinate with metal ions (Mn2+, Co2+, Fe3+, Cu2+and Ni2+). Thirteen new Schiff base complexes were prepared in this section(seven copper (II ) complexes and six nickel( II) complexes). Under the pressure of N2, to a refluxing solution of Schiff base in dry ethanol, metal ion solution was added dropwise and refluxing was continued over next 3h, then filtrated and the crude product was purified by recrystallized. At last, we got two types of metal complexes: eight copper( II) complexes and six nickel( II ) complexes. All these compounds were characterized by IR, UV, MS and elemental analyses.
本论文研究了目前未见国内外文献报道的、水杨醛中苯环上含有取代基的水杨醛缩脱氢枞胺Schiff碱及其金属配合物的合成与表征，共计获得了21个新的化合物，从而为后期生物活性的测定及不对称催化提供研究基础和实验样品。
在Schiff碱的合成中，我们以无水乙醇为溶剂，利用醛与氨基能够发生氨解反应的性质，在加热条件下，将系列取代水杨醛(水杨醛、5-氯水杨醛、5-硝基水杨醛、5-溴水杨醛、3，5-二氯水杨醛、3，5-二溴水杨醛、4-羟基水杨醛、4-二乙氨基水杨醛、4-甲氧基水杨醛)的乙醇溶液滴加到脱氢枞胺-乙醇溶液中，经缩合得到9个Schiff碱，其中8个Schiff碱未见文献报道。通过IR、UV、~1HNMR、MS及元素分析等手段，对新Schiff碱进行了表征。
利用Schiff碱能够与金属离子配位的性质，我们选取了Mn~(2+)、Co~(2+)、Fe~(3+)、Cu~(2+)和Ni~(2+)离子与系列Schiff碱进行配位。反应以无水乙醇为溶剂，在N_2氛围下，分别将Mn~(2+)、Co~(2+)、Fe~(3+)、Cu~(2+)和Ni~(2+)的乙醇溶液缓慢滴加到热的Schiff碱-KOH溶液中。反应最终得到了8个铜系Schiff碱配合物和6个镍系配合物。其中镍系配合物和7个铜系配合物未见文献报道。用IR、UV、MS及元素分析等手段对配合物进行了表征，结果表明亚胺基上的N原子及酚羟基上的氧原子参与了金属离子的配位，形成了N，N，O，O四配位的铜、镍配合物。
Dehydroabietylamine is a kind of optical active amine, which derived from dehydroabietic acid. Thus dehydroabietylamine and its acetates have showed some bioactivities such as pesticide, bactericide and algaecide. It is a sort of important forestry product, which can be applied in papermaking, medicine, pesticide, chemical industries etc. It can also be used as chiral resolution agent. With the properties of bioactivities and asymmetric catalytic activities, the research of Schiff bases and their complexes is also one of the active fields.
Our main research work has been focused on the synthesis, characterization of substituted salicylaldehyde Schiff bases and their complexes, which are not reported in articles now. There are twenty-one new compounds in total.
Nine Schiff bases were prepared by condensation of amine with substituted salicylaldehydes. To a solution of chiral amine (dehydroabietylamine) in dry ethanol, substituted salicylaldehyde-ethanol solution was added and the mixture was refluxed for 3h, then filtrated or evaporated the solvent. Some Schiff bases were purified by recrystallized. In this section, eight compounds are not reported in articles. Some new Schiff bases were characterized by IR, UV,1HNMR and elemental analyses.
These Schiff bases are normally bidentate ligands, which can provide O and N atoms to coordinate with metal ions (Mn2+, Co2+, Fe3+, Cu2+and Ni2+). Thirteen new Schiff base complexes were prepared in this section(seven copper (II ) complexes and six nickel( II) complexes). Under the pressure of N2, to a refluxing solution of Schiff base in dry ethanol, metal ion solution was added dropwise and refluxing was continued over next 3h, then filtrated and the crude product was purified by recrystallized. At last, we got two types of metal complexes: eight copper( II) complexes and six nickel( II ) complexes. All these compounds were characterized by IR, UV, MS and elemental analyses.
引文
1 Mishra, AP, Srivastava SK, Srivastava, et al. Synthesis, characterization and antibacterial activity of some 3d-metal complexes with thiophene-2-aldehyde-4-chloro/bromoaniline. J Indian Chem Soc, 1997, 74(6): 487—488
2 Nath M, Yadav R. Spectral studies and in vitro antimicrobial activity of new organotin(Ⅳ) complex of Schiff bases derived from amino acids. Bull Chem Soc Jpn 1997, 70(6): 1331—1337
3 Nath M, Goyal S, Goyal S.Synthesis, spectral and biological studies of organosilicon(Ⅳ) complexes of Schiff bases derived from amino acids. Synth React Inorg Met-Org. Chem, 2000, 30(9): 1791—1804
4 Chohan ZH, Praveen M, Ghaffar A.Structural and biological behavior of Co(Ⅱ),Cu(Ⅱ) and Ni(Ⅱ) metal complexes of some amino acid derived Schiff-bases. Met-Based Drugs, 1997,4(5):267-272
5 Chohan ZH, Praveen M. Biological role of anions (sulfate, nitrate, oxalate and acetate) on the antibacterial properties of cobalt(Ⅱ) and nickel(Ⅱ) complexes with pyrazinedicarboxamide derived, furanyl and thienyl compounds. Met-Based Drugs, 1999, 6(2): 95-99
6 Chohan ZH, Praveen M. Synthesis, characterization, coordination and antibacterial properties of novel asymmetric 1, 1'-disubstituted ferrocene-derived Schiff base ligands and their Co(Ⅱ), Cu(Ⅱ), Ni(Ⅱ) and Zn(Ⅱ) complexes. Appl Organoment Chem, 2001, 15(7): 617—625
7 Bolos GA, Nikolov GS, Ekateriniadou L, et al. Structure-activity relationships for some diamine, triamine and Schiff bases derivatives and their copper(Ⅱ) complexes. Met-Based Drugs, 1998, 5(6):323—332
8 Rashan LJ, Aziz AA, Sulayman, KD, et al. Antibacterial activity of diorganotin(Ⅳ) complexes of some Schiff-base derivatives. Asian J Chem, 1998, 10(2):338—341
9 Viswanathamurthi P, Dharmaraj N, Anuradha S, et al. Ruthenium (Ⅲ) complexes with tetradentate Schiff bases containing triphenylphosphine or triphenylarsine. Transition Met Chem, 1998, 23(4): 337-341
10 Bi SW, Li GZ. Synthesis, characterization and antifungal activity of some transition metal complexes of the Schiff bases derived from 4-acetylbiphenyl and S-benzyldithiocarbazate. Synth React Inorg Met-Org Chem, 1999, 29(10): 1829—1841
11 Pandeya SN, Sriram D, Nath G, et al. Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine. Farmaco, 1999, 54(9): 624-628
12 Karia FD, Parsania PH. Synthesis, biological and thermal propertiesof Schiff bases of bisphenol-C. Asia J Chem, 1999, 11(3): 991～995
13 Rathod AS, Berad BN, Doshi AG. Synthesis of Schiff bases from 2-amino-4-phenylthiazole and substituted 2-aminobenzothiazoles and their antimicrobial activity. Orient J Chem, 2000, 16(3): 549-552
14 Idrees M, Siddique M, Patil SD, et al. Synthesis of Schiff bases of thiophene-2-carboxaldehyde and its antimicrobial activity. Orient J Chem, 2001, 17(1): 131-133
15 李锦州，于文锦，李刚．噻吩甲酰基吡唑啉酮缩乙二胺稀土配合物．应用化学，2000，17(3)：280-283
16 李锦州，李刚，于文锦．呋喃甲酰基吡唑啉酮双席夫碱稀土配合物的合成、表征及生物活性．中国稀土学报，2000，18(1)：71-73
17 Mohan S, Saravanan J. Synthesis and antibacterial activity of some Schiff's bases of 2-amino-3-(N-o-tolylcarboxamido)-4,5-dimethylthiophene. Indian Journal of Heterocyclic Chemistry,2002, 12(1): 87—88
18 Calis U, Yarim M, Koksal M, et al. Synthesis and antimicrobial activity evaluation of some new adamantine derivatives. Arzneimittel-Forschung,2002, 52(10):778—781
19 Tarafder MTH, Kasbollah A, Saravanan N, et al. S-methyldithiocarbazate and its Schiff base: evaluation of bondings and biological properties. Journal of Biochemistry, Molecular Biology and Biophysics,2002, 6(2):85—91
20 Das A, Trousdale MD, Ren S, et al. Inhibition of herpes simplex virus type 1 and adenovirus type 5 by heterocyclic Schiff bases of aminohydroxyguanidine tosylate. Antiviral Res, 1999, 44(3):201-208
21 Lin JM, Xu LL. Synthesis of γ-N-[(halobenzylideneaminoethyl)-aminoethyl]aminopropyl-2,8,9-trioxas-5-aza-1-silabic yclo[3,3,3]-undecanes. Synth React Ingor Met-Org Chem, 1997, 27(3): 419-430
22 Pathak P, Jolly YS, Sharma KP. Synthesis and biological activities of some new substituted aarylazo Schiff bases. Orient J Chem, 2000, 16(1): 161-162
23 Offiong OE, Nfor E, Avi AA, et al. Synthesis, spectral and cytoxicity studies of palladium(Ⅱ) and platinum(Ⅱ) amino acid Schiff bases complexes. Transition Met Chem,2000; 25(4):369—373
24 陈琪，朱海亮，戚穗坚，等．六氮杂大环希夫碱与银(Ⅰ)系列配合物的抗肿瘤活性研究．中山大学学报(自然科学版)2001，40(2)，65-67
25 唐宏武，陈蓓，陈观铨，等．吖啶橙-细胞DNA荧光抑制法初步筛选抗癌药物的研究．武汉大学学报(自然科学版)，1997，43(6)：711-716
26 谢雨礼，宋琳，朱勤，等．酚取代双膦酸酯Schiff碱的合成及抗癌活性研究．中国药物化学杂志，2000．10(2)：88—91
27 徐莉，徐世平．2-吲哚醛西佛碱化合物的合成及其抗癌活性研究．药学学报，2000，35(4)：269-272
28 Tofazzal M, Tarafder H, Ali AM, et al. Coordination chemistry and biological activity of
bidentate and quadridentate nitrogen-sulfur donor ligands and their complexes. Transition Met Chem,2000, 25(6):706—710
29 Tarafder MTH, Kasbollah A, Crouse KA, et al. Synthesis and characterization of Zn(Ⅱ) and Cd(Ⅱ) complexes of S-benzyl-β-N-(2-pyridyl)methylenedithiocarbazate(HNNS):bioactivity of the HNNS Schiff base and its Zn(Ⅱ), Cu(Ⅱ) and Cd(Ⅱ) complex. Polyhedron, 2001, 20(18):2363—2370
30 Tarafder MTH, Jin KT, Crouse KA, et al. Coordination chemistry and bioactivity of Ni~(2+), Cu~(2+), Cd~(2+) and Zn~(2+) complexes containing bidentate Schiff bases derived from S-benzyldithiocarbazate and the X-ray crystal structure of bis[S-benzyl-β-N-(5-methyl-2-furylmethylene) dithiocarbazato] Cadmium(Ⅱ). Polyhedron, 2002, 21(26):2547-2554
31 Kubo I, Kinst-Hori I. Tyrosmase inhibition activity of the olive oil flavor compounds. J Agric Food Chem, 1999, 47(11):4574-4578
32 Scozzafava A, Banciu MD, Popescu A, et al. Carbonic anhydrase inhibitors: Part 90. Synthesis of Schiff bases of hydroxybenzaldehydes with aromatic sulfonamides and their reactions with arylsulfonyl isocyanates. J Enzyme Inhib, 2000, 15(6):533-546
33 汪焱钢，曹蕾，杨军，等．具有植物激素活陸的Schiff碱化合物的研究(Ⅲ)-噻二唑类Schiff碱的合成及其生物活性．高等学校化学学报，1999，20(12)：1903-1905
34 芦冰熙，李淑贤，叶文法，等．含四唑环Schiff碱的合成与植物激素活性．湖南化，2000，30(5)：42-43
35 Mazitova AK, Khamaev VK, Sukhareva IA, et al. Preparation of 5-(methyleneimino)-3,6-dimethyl-1,2,4-triazines having growth-regulating and herbicidal activity by the Schiff-base formation of aldehydes with 5-amino-3,6-dimethyl-1,2,4-triazine. RU 2146251, 2000-03-10
36 Mazitova AK, Khamaev VK, Aminova GK, et al. Preparation of 6-methyl-1,2,4-triazine-5-one azomethines having plant growth-regulating and herbicidal activity by formation of Schiff bases from aldehydes and 3-amino-6-methyl-1,2,4-triazine-5-one. RU 2146252, 2000-03-10
37 Samadhiya S, Halve A. Synthetic utility of Schiff bases an potential herbicidal agents. Orient J Chem, 2001, 17(1):119-122
38 Das BP, Choudhurry TR, Das J. Larvicidal activity of some heterocylic compounds and aromatic nitro compounds. Environ Ecol, 1997,15(4): 838-842
39 黎红梅，袁均林，宋发辉，等．甲胺磷席夫碱及其金属配合物的合成与生物活性研究．华中师范大学学报(自然科学版)，2001，35(4)：420—423
40 Bharti N, Maurya MR, Naqvi F, et al. Synthesis and antiamoebic activity of new cyclocotadiene ruthenium(Ⅱ) complexes with 2-acetylpyridine and benzimidazole derivatives. Bioorg. Med Chem Lett, 2000, 10(20):2243-2245
41 Neelam B, Mannar MR, Fehmida N, et al. Palladium(Ⅱ) complexes of NS donor ligands
derived from S-benzyldithilcarbazate and thiosemicarbazide as antiamoebic agents. Eur J Med Chem, 2000, 35(5): 481-486
42 Thomas JM, Toshihiko TS, Harry BG, et al. Cobalt Schiffbase compounds. US 6008190, 1999-12-28
43 Bernard MC, Arlington MA, Susan D, et al. Cyclic salen-metal compositions: reactive oxygen species scavengers useful as antioxidants in the treatment and prevention of diseases. US 6589948 B1, 2003-07-08
44 Yousef AA, Locust V, Richard JB, et al. Compounds having MIF antagonist activity. US6599938 B1, 2003-07-29
45 赵元弟，庞代文，王宗礼，等．抗癌药物的电化学研究Ⅰ一种Fe(Ⅲ)Schiff碱配合物的基本电化学性质．化学学报，1998，56(2)：178-183
46 倪瑾，孟祥顺，蔡建明，等．Schiff碱稀土金属配合物对辐射导致肿瘤细胞DNA损伤及修复的影响．中华放射医学与防护杂志，2000，20(1)：46-49
47 孙伟，夏春谷，手性金属Salen配合物在不对称催化中的应用 化学进展 2002，1，8
48 Sigma MS, Jacobsen E. N, J. Am. Chem. Soc., 1998, 120, 5315
49 Zhang W, Loebach J L, Wilson S R, Jacobsen E N, J. Am. Chem. Soc., 1990, 112: 2801-2804
50 Irie R, Noda K, Ito Y, Matsumoto N, Katsuki T. Tetrahedron Lett., 1990, 31:7345-7348
51 林国强，陈耀全，陈新滋，等．手性合成——不对称反应及其应用，北京：科学出版社，186．
52 Li LS, Wu YK, Hu YJ, et al. Tetrahedron: Asymm., 1998, 9, 2271
53 Schaus SE, Bran& J, Jacobsen EN, J. Org. Chem., 1998, 63,403
54 孙伟，夏春谷．手性金属Salen配合物在不对称催化中的应用化学进展 2002，1，9
55 Niimi T, Uchida T, Irie R, et al. Tetrahedron Lett., 2000, 41:3647-3651
56 Tokungana M, Larrow JF, Kakiuchi F, et al. Science, 1997, 227,936
57 王胜国，于国清，王世文．不对称催化及其在精细化工中的应用工业催化 2000，4，12
58 张鹏荣，龚勇华，聂娟．不对称催化化学教学 2002，2，23
59 程芝主编．天然树脂生产工艺学．
60 曾昭琼主编．有机化学，高等教育出版社，322．
61 董慧茹主编．仪器分析，化学工业出版社，143，213．
62 荣国斌译，朱士正校．波谱数据表．有机化合物的结构解析．华东理工大学出版社
63 施耀曾，孙祥祯，蒋燕灏，等．有机化合物光谱和化学鉴定．江苏科学技术出版社，169-170．
64 Andrzej V, Stanislaw W, Ram L, et al.Synthesis and characterization of nickel(Ⅱ),copper(Ⅱ),manganese(Ⅲ) and iron(Ⅲ) complexes with new chiral salen-type
ligand {N,N'-bis(3,5-di-tert-butylsalicylidene)-(1R,3S)-1,3-diamine-1,2,2-trimethylcyclo pentane}. Polyhedron, 1998, 17(8): 1231-1240.
65 张祥麟，康衡主编配位化学，中南工业大学出版社．6-7
66 北京师范大学，华中师范大学，南京师范大学无机化学教研室编无机化学(第二版)713
67 罗勤慧，沈孟长编配位化学，江苏科学技术出版社．117，128-129
68 邸欣，钟大放．电喷雾质谱法的理论与实践．沈阳药科大学学报，1999，16(2)：146-150
69 徐宝军，郑毅男，崔勐，等．电喷雾串联质谱法鉴定桔梗皂苷D~1．中国药物化学杂志，2000，10(3)：193-196
70 陈益，苗志伟，付华，等．核苷5’-硫代磷酰氨基酸酯的电喷雾质谱研究．质谱学报，21(3，4)：107-108
71 金燕，王小淳．HPLC／ESI-MS分析脂肪醇聚氧乙烯醚中碳链及EO数分布．2000，21(2)：66-72
72 陈秋云，李长江，胡学雷．Gd(Ⅲ)-Cu(Ⅱ)杂核大环配合物的合成、表征和磁性．2002，20(增刊)：26-29
73 马理，宋凤瑞，刘子阳，等．金属卟啉及其与与咪唑络合物的电喷雾质谱研究．分析化学，2001，29(5)：573-576
74 孙伟，夏春谷，赵培庆．手性Salen-Co(Ⅱ)配合物不对称催化苯乙酮硼氢化反应研究．化学学报，2001，59(6)：976-978
2 Nath M, Yadav R. Spectral studies and in vitro antimicrobial activity of new organotin(Ⅳ) complex of Schiff bases derived from amino acids. Bull Chem Soc Jpn 1997, 70(6): 1331—1337
3 Nath M, Goyal S, Goyal S.Synthesis, spectral and biological studies of organosilicon(Ⅳ) complexes of Schiff bases derived from amino acids. Synth React Inorg Met-Org. Chem, 2000, 30(9): 1791—1804
4 Chohan ZH, Praveen M, Ghaffar A.Structural and biological behavior of Co(Ⅱ),Cu(Ⅱ) and Ni(Ⅱ) metal complexes of some amino acid derived Schiff-bases. Met-Based Drugs, 1997,4(5):267-272
5 Chohan ZH, Praveen M. Biological role of anions (sulfate, nitrate, oxalate and acetate) on the antibacterial properties of cobalt(Ⅱ) and nickel(Ⅱ) complexes with pyrazinedicarboxamide derived, furanyl and thienyl compounds. Met-Based Drugs, 1999, 6(2): 95-99
6 Chohan ZH, Praveen M. Synthesis, characterization, coordination and antibacterial properties of novel asymmetric 1, 1'-disubstituted ferrocene-derived Schiff base ligands and their Co(Ⅱ), Cu(Ⅱ), Ni(Ⅱ) and Zn(Ⅱ) complexes. Appl Organoment Chem, 2001, 15(7): 617—625
7 Bolos GA, Nikolov GS, Ekateriniadou L, et al. Structure-activity relationships for some diamine, triamine and Schiff bases derivatives and their copper(Ⅱ) complexes. Met-Based Drugs, 1998, 5(6):323—332
8 Rashan LJ, Aziz AA, Sulayman, KD, et al. Antibacterial activity of diorganotin(Ⅳ) complexes of some Schiff-base derivatives. Asian J Chem, 1998, 10(2):338—341
9 Viswanathamurthi P, Dharmaraj N, Anuradha S, et al. Ruthenium (Ⅲ) complexes with tetradentate Schiff bases containing triphenylphosphine or triphenylarsine. Transition Met Chem, 1998, 23(4): 337-341
10 Bi SW, Li GZ. Synthesis, characterization and antifungal activity of some transition metal complexes of the Schiff bases derived from 4-acetylbiphenyl and S-benzyldithiocarbazate. Synth React Inorg Met-Org Chem, 1999, 29(10): 1829—1841
11 Pandeya SN, Sriram D, Nath G, et al. Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine. Farmaco, 1999, 54(9): 624-628
12 Karia FD, Parsania PH. Synthesis, biological and thermal propertiesof Schiff bases of bisphenol-C. Asia J Chem, 1999, 11(3): 991～995
13 Rathod AS, Berad BN, Doshi AG. Synthesis of Schiff bases from 2-amino-4-phenylthiazole and substituted 2-aminobenzothiazoles and their antimicrobial activity. Orient J Chem, 2000, 16(3): 549-552
14 Idrees M, Siddique M, Patil SD, et al. Synthesis of Schiff bases of thiophene-2-carboxaldehyde and its antimicrobial activity. Orient J Chem, 2001, 17(1): 131-133
15 李锦州，于文锦，李刚．噻吩甲酰基吡唑啉酮缩乙二胺稀土配合物．应用化学，2000，17(3)：280-283
16 李锦州，李刚，于文锦．呋喃甲酰基吡唑啉酮双席夫碱稀土配合物的合成、表征及生物活性．中国稀土学报，2000，18(1)：71-73
17 Mohan S, Saravanan J. Synthesis and antibacterial activity of some Schiff's bases of 2-amino-3-(N-o-tolylcarboxamido)-4,5-dimethylthiophene. Indian Journal of Heterocyclic Chemistry,2002, 12(1): 87—88
18 Calis U, Yarim M, Koksal M, et al. Synthesis and antimicrobial activity evaluation of some new adamantine derivatives. Arzneimittel-Forschung,2002, 52(10):778—781
19 Tarafder MTH, Kasbollah A, Saravanan N, et al. S-methyldithiocarbazate and its Schiff base: evaluation of bondings and biological properties. Journal of Biochemistry, Molecular Biology and Biophysics,2002, 6(2):85—91
20 Das A, Trousdale MD, Ren S, et al. Inhibition of herpes simplex virus type 1 and adenovirus type 5 by heterocyclic Schiff bases of aminohydroxyguanidine tosylate. Antiviral Res, 1999, 44(3):201-208
21 Lin JM, Xu LL. Synthesis of γ-N-[(halobenzylideneaminoethyl)-aminoethyl]aminopropyl-2,8,9-trioxas-5-aza-1-silabic yclo[3,3,3]-undecanes. Synth React Ingor Met-Org Chem, 1997, 27(3): 419-430
22 Pathak P, Jolly YS, Sharma KP. Synthesis and biological activities of some new substituted aarylazo Schiff bases. Orient J Chem, 2000, 16(1): 161-162
23 Offiong OE, Nfor E, Avi AA, et al. Synthesis, spectral and cytoxicity studies of palladium(Ⅱ) and platinum(Ⅱ) amino acid Schiff bases complexes. Transition Met Chem,2000; 25(4):369—373
24 陈琪，朱海亮，戚穗坚，等．六氮杂大环希夫碱与银(Ⅰ)系列配合物的抗肿瘤活性研究．中山大学学报(自然科学版)2001，40(2)，65-67
25 唐宏武，陈蓓，陈观铨，等．吖啶橙-细胞DNA荧光抑制法初步筛选抗癌药物的研究．武汉大学学报(自然科学版)，1997，43(6)：711-716
26 谢雨礼，宋琳，朱勤，等．酚取代双膦酸酯Schiff碱的合成及抗癌活性研究．中国药物化学杂志，2000．10(2)：88—91
27 徐莉，徐世平．2-吲哚醛西佛碱化合物的合成及其抗癌活性研究．药学学报，2000，35(4)：269-272
28 Tofazzal M, Tarafder H, Ali AM, et al. Coordination chemistry and biological activity of
bidentate and quadridentate nitrogen-sulfur donor ligands and their complexes. Transition Met Chem,2000, 25(6):706—710
29 Tarafder MTH, Kasbollah A, Crouse KA, et al. Synthesis and characterization of Zn(Ⅱ) and Cd(Ⅱ) complexes of S-benzyl-β-N-(2-pyridyl)methylenedithiocarbazate(HNNS):bioactivity of the HNNS Schiff base and its Zn(Ⅱ), Cu(Ⅱ) and Cd(Ⅱ) complex. Polyhedron, 2001, 20(18):2363—2370
30 Tarafder MTH, Jin KT, Crouse KA, et al. Coordination chemistry and bioactivity of Ni~(2+), Cu~(2+), Cd~(2+) and Zn~(2+) complexes containing bidentate Schiff bases derived from S-benzyldithiocarbazate and the X-ray crystal structure of bis[S-benzyl-β-N-(5-methyl-2-furylmethylene) dithiocarbazato] Cadmium(Ⅱ). Polyhedron, 2002, 21(26):2547-2554
31 Kubo I, Kinst-Hori I. Tyrosmase inhibition activity of the olive oil flavor compounds. J Agric Food Chem, 1999, 47(11):4574-4578
32 Scozzafava A, Banciu MD, Popescu A, et al. Carbonic anhydrase inhibitors: Part 90. Synthesis of Schiff bases of hydroxybenzaldehydes with aromatic sulfonamides and their reactions with arylsulfonyl isocyanates. J Enzyme Inhib, 2000, 15(6):533-546
33 汪焱钢，曹蕾，杨军，等．具有植物激素活陸的Schiff碱化合物的研究(Ⅲ)-噻二唑类Schiff碱的合成及其生物活性．高等学校化学学报，1999，20(12)：1903-1905
34 芦冰熙，李淑贤，叶文法，等．含四唑环Schiff碱的合成与植物激素活性．湖南化，2000，30(5)：42-43
35 Mazitova AK, Khamaev VK, Sukhareva IA, et al. Preparation of 5-(methyleneimino)-3,6-dimethyl-1,2,4-triazines having growth-regulating and herbicidal activity by the Schiff-base formation of aldehydes with 5-amino-3,6-dimethyl-1,2,4-triazine. RU 2146251, 2000-03-10
36 Mazitova AK, Khamaev VK, Aminova GK, et al. Preparation of 6-methyl-1,2,4-triazine-5-one azomethines having plant growth-regulating and herbicidal activity by formation of Schiff bases from aldehydes and 3-amino-6-methyl-1,2,4-triazine-5-one. RU 2146252, 2000-03-10
37 Samadhiya S, Halve A. Synthetic utility of Schiff bases an potential herbicidal agents. Orient J Chem, 2001, 17(1):119-122
38 Das BP, Choudhurry TR, Das J. Larvicidal activity of some heterocylic compounds and aromatic nitro compounds. Environ Ecol, 1997,15(4): 838-842
39 黎红梅，袁均林，宋发辉，等．甲胺磷席夫碱及其金属配合物的合成与生物活性研究．华中师范大学学报(自然科学版)，2001，35(4)：420—423
40 Bharti N, Maurya MR, Naqvi F, et al. Synthesis and antiamoebic activity of new cyclocotadiene ruthenium(Ⅱ) complexes with 2-acetylpyridine and benzimidazole derivatives. Bioorg. Med Chem Lett, 2000, 10(20):2243-2245
41 Neelam B, Mannar MR, Fehmida N, et al. Palladium(Ⅱ) complexes of NS donor ligands
derived from S-benzyldithilcarbazate and thiosemicarbazide as antiamoebic agents. Eur J Med Chem, 2000, 35(5): 481-486
42 Thomas JM, Toshihiko TS, Harry BG, et al. Cobalt Schiffbase compounds. US 6008190, 1999-12-28
43 Bernard MC, Arlington MA, Susan D, et al. Cyclic salen-metal compositions: reactive oxygen species scavengers useful as antioxidants in the treatment and prevention of diseases. US 6589948 B1, 2003-07-08
44 Yousef AA, Locust V, Richard JB, et al. Compounds having MIF antagonist activity. US6599938 B1, 2003-07-29
45 赵元弟，庞代文，王宗礼，等．抗癌药物的电化学研究Ⅰ一种Fe(Ⅲ)Schiff碱配合物的基本电化学性质．化学学报，1998，56(2)：178-183
46 倪瑾，孟祥顺，蔡建明，等．Schiff碱稀土金属配合物对辐射导致肿瘤细胞DNA损伤及修复的影响．中华放射医学与防护杂志，2000，20(1)：46-49
47 孙伟，夏春谷，手性金属Salen配合物在不对称催化中的应用 化学进展 2002，1，8
48 Sigma MS, Jacobsen E. N, J. Am. Chem. Soc., 1998, 120, 5315
49 Zhang W, Loebach J L, Wilson S R, Jacobsen E N, J. Am. Chem. Soc., 1990, 112: 2801-2804
50 Irie R, Noda K, Ito Y, Matsumoto N, Katsuki T. Tetrahedron Lett., 1990, 31:7345-7348
51 林国强，陈耀全，陈新滋，等．手性合成——不对称反应及其应用，北京：科学出版社，186．
52 Li LS, Wu YK, Hu YJ, et al. Tetrahedron: Asymm., 1998, 9, 2271
53 Schaus SE, Bran& J, Jacobsen EN, J. Org. Chem., 1998, 63,403
54 孙伟，夏春谷．手性金属Salen配合物在不对称催化中的应用化学进展 2002，1，9
55 Niimi T, Uchida T, Irie R, et al. Tetrahedron Lett., 2000, 41:3647-3651
56 Tokungana M, Larrow JF, Kakiuchi F, et al. Science, 1997, 227,936
57 王胜国，于国清，王世文．不对称催化及其在精细化工中的应用工业催化 2000，4，12
58 张鹏荣，龚勇华，聂娟．不对称催化化学教学 2002，2，23
59 程芝主编．天然树脂生产工艺学．
60 曾昭琼主编．有机化学，高等教育出版社，322．
61 董慧茹主编．仪器分析，化学工业出版社，143，213．
62 荣国斌译，朱士正校．波谱数据表．有机化合物的结构解析．华东理工大学出版社
63 施耀曾，孙祥祯，蒋燕灏，等．有机化合物光谱和化学鉴定．江苏科学技术出版社，169-170．
64 Andrzej V, Stanislaw W, Ram L, et al.Synthesis and characterization of nickel(Ⅱ),copper(Ⅱ),manganese(Ⅲ) and iron(Ⅲ) complexes with new chiral salen-type
ligand {N,N'-bis(3,5-di-tert-butylsalicylidene)-(1R,3S)-1,3-diamine-1,2,2-trimethylcyclo pentane}. Polyhedron, 1998, 17(8): 1231-1240.
65 张祥麟，康衡主编配位化学，中南工业大学出版社．6-7
66 北京师范大学，华中师范大学，南京师范大学无机化学教研室编无机化学(第二版)713
67 罗勤慧，沈孟长编配位化学，江苏科学技术出版社．117，128-129
68 邸欣，钟大放．电喷雾质谱法的理论与实践．沈阳药科大学学报，1999，16(2)：146-150
69 徐宝军，郑毅男，崔勐，等．电喷雾串联质谱法鉴定桔梗皂苷D~1．中国药物化学杂志，2000，10(3)：193-196
70 陈益，苗志伟，付华，等．核苷5’-硫代磷酰氨基酸酯的电喷雾质谱研究．质谱学报，21(3，4)：107-108
71 金燕，王小淳．HPLC／ESI-MS分析脂肪醇聚氧乙烯醚中碳链及EO数分布．2000，21(2)：66-72
72 陈秋云，李长江，胡学雷．Gd(Ⅲ)-Cu(Ⅱ)杂核大环配合物的合成、表征和磁性．2002，20(增刊)：26-29
73 马理，宋凤瑞，刘子阳，等．金属卟啉及其与与咪唑络合物的电喷雾质谱研究．分析化学，2001，29(5)：573-576
74 孙伟，夏春谷，赵培庆．手性Salen-Co(Ⅱ)配合物不对称催化苯乙酮硼氢化反应研究．化学学报，2001，59(6)：976-978