摘要
松香是多种树脂酸和少量脂肪酸、中性物质的混合物，其中树脂酸是主要成分，约占其总量的90%以上。松香是我国重要林产资源，产量居世界第一位。松香的深加工产品不仅可以用于造纸、油漆、肥皂、油墨等传统工业领域，还可以用于生物医药领域。
脱氢枞胺是一种具有三环菲结构的松香改性产品，它也是歧化松香胺的主要成分。将脱氢枞胺与（取代）苯甲酰氯反应，合成一系列酰胺类衍生物，并在其B环和C环上通过氧化、硝化、成肟、还原等方法引入羰基、硝基、肟基及羟基等官能团。对脱氢枞胺的氨基进行改造，引入了羧甲基。用IR、~1H NMR、~(13)C NMR、MS及HRMS等对所合成的新型脱氢枞胺衍生物进行了结构表征。对脱氢枞胺衍生物进行了抗癌、雄激素受体（AR）结合活性、α1A肾上腺素受体拮抗/激动活性、细胞分裂周期磷酸酯酶Cdc25B抑制活性、血管内皮生长因子受体（KDR）抑制活性、抗菌活性的测试，并对构效关系进行了研究和总结。采用饱和溶液法制备了脱氢枞胺（4-羟基）水杨醛Schiff碱β-环糊精包合物，并对包合物进行了结构鉴定和抗癌活性测试。通过对数据的整理归纳，现得到如下结论：
（1）以歧化松香胺为原料，与对甲苯磺酸反应，采用成盐法提纯制备了脱氢枞胺，产率为63.7%。脱氢枞胺与（取代）苯甲酰氯的反应，合成了N-苯甲酰基-脱氢枞胺及其类似物（2a~2d），产率为68.4~72.8%。
（2）采用硝酸铜-乙酸酐体系对脱氢枞胺衍生物的C环进行硝化，在12位引入硝基，得到N-苯甲酰基-12-硝基脱氢枞胺及其类似物（3a~3d），产率为69.6~74.8%。相对于传统的浓硫酸-浓硝酸的混酸体系，本实验中使用硝酸铜-乙酸酐体系进行硝化，具有反应较为缓和、选择性好等特点。
（3）利用100~200目的粗孔硅胶作载体，负载三氧化铬制备了一种CrO_3/SiO_2固载氧化试剂，研究了CrO_3/SiO_2对N-苯甲酰基-脱氢枞胺（2a）定向氧化制备N-苯甲酰基-脱氢枞胺-7-酮（4a）的反应，考察了溶剂种类、溶剂量、反应温度、负载量及氧化剂用量对产率的影响。结果表明，采用负载量为2.0mmol/g的CrO_3/SiO_2固载氧化剂，氧化剂用量为N-苯甲酰基-脱氢枞胺及其类似物（2a~2d，3a）的2倍摩尔量，以50mL环己烷为溶剂，回流温度下搅拌反应8h，对2.57mmol的N-苯甲酰基-脱氢枞胺及其类似物（2a~2d，3a）进行氧化，可在B环的7号位引入羰基，得到N-苯甲酰基-脱氢枞胺-7-酮及其类似物（4a~4e），产率为53.0~60.2%。相对于传统的CrO_3/CH_3COOH液相体系，使用CrO_3/SiO_2固载氧化试剂的产物后处理过程更为简单快捷。CrO_3/SiO_2固载氧化试剂的制备及产物分离提纯过程均不产生铬废液，具有一定的环保意义。
（4）使用盐酸羟胺将脱氢枞胺衍生物B环7号位羰基成肟，得N-苯甲酰基-脱氢枞胺-7-肟及其类似物（5a~5d），产率为80.6~85.3%；使用硼氢化钠将B环7号位羰基还原成羟基，得N-苯甲酰基-脱氢枞胺-7-醇（6a）和N-（2-氯苯甲酰基）-脱氢枞胺-7-醇（6c），产率分别为84.3%和83.2%。
（5）以脱氢枞胺和氯乙酸为原料，在碱性条件下，制备了N，N-二羧甲基脱氢枞胺（7）和N-羧甲基脱氢枞胺（钾盐）（8），产率分别为58.3%和53.0%，反应体系pH值的调节为本实验的关键。
（6）采用MTT法测试了脱氢枞胺衍生物（2a、2c、2d、3a、3c、3d、4a、4c和4d）对前列腺癌细胞PC-3和卵巢癌细胞Hey-1B的抗癌活性，化合物对PC-3的IC50为5.7~84.9μg/mL，对Hey-1B的IC50为11.3~129.8μg/mL。通过对构效关系的研究发现，脱氢枞胺衍生物B环的7号位和C环的12号位可能是十分重要的活性位点，对抗癌活性的影响较大。在B环的7号位引入羰基或在C环的12号位引入硝基，可增加部分化合物对PC-3和Hey-1B的抗癌活性。例如，B环7号位含有羰基的N-苯甲酰基-脱氢枞胺-7-酮（4a），对前列腺癌细胞株PC-3和卵巢癌细胞株Hey-1B的IC50只有其母体化合物N-苯甲酰基-脱氢枞胺（2a）的9.1%和26.0%；C环12号位含有硝基的N-苯甲酰基-12-硝基脱氢枞胺（3a），对前列腺癌细胞株PC-3和卵巢癌细胞株Hey-1B的IC50只有其母体化合物N-苯甲酰基-脱氢枞胺（2a）的13.1%和18.3%。
（7）采用MTT法测试了部分脱氢枞胺衍生物对人肝癌细胞HepG2和正常肝细胞L02的毒性，结果表明，N-（4-硝基苯甲酰基）-12-硝基脱氢枞胺（3d）和N-苯甲酰基-脱氢枞胺-7-酮（4a）对人肝癌细胞HepG2具有较好的杀伤活性，而对正常肝细胞L02的毒性较小。
（8）采用体外配体受体竞争结合实验测定了脱氢枞胺衍生物的雄激素受体（AR）结合活性，结果表明，在初始浓度为10μmol/L时，N-苯甲酰基-脱氢枞胺-7-酮（4a）与AR具有一定的结合活性，IC50为83.8nmol/L。
（9）采用钙流筛选方法测试了化合物的α1A肾上腺素受体拮抗/激动活性，结果表明，在浓度为10μmol/L时，N-苯甲酰基-脱氢枞胺-7-肟（5a）在α1A肾上腺素受体上约有25%的拮抗作用；N-（2-氯苯甲酰基）-脱氢枞胺-7-酮（4c）、N-（4-硝基苯甲酰基）-脱氢枞胺-7-酮（4d）、N-苯甲酰基-12-硝基脱氢枞胺-7-酮的合成（4e）在α1A肾上腺素受体上约有45~50%的拮抗作用。
（10）采用均相时间分辨荧光（HTRF）法研究化合物的血管内皮生长因子受体（KDR）抑制活性，结果表明，在浓度为4×10~-4mol/L时，所有测试的化合物均有一定的KDR抑制活性，抑制率38.27~99.34%。其中，N-苯甲酰基-脱氢枞胺-7-酮（4a）、N-（4-硝基苯甲酰基）-脱氢枞胺-7-酮（4d）、脱氢枞胺（3，4-二羟基）水杨醛Schiff碱（LIN110）、N-（2-羟基）-苄基-脱氢枞胺盐酸盐（LIN402）、N（-5-硝基-2-羟基）-苄基-脱氢枞胺盐酸盐（LIN404）、12，14-二硝基脱氢枞胺（4-羟基）苯甲醛Schiff碱（LIN609）以及12-硝基脱氢枞胺（5-硝基）水杨醛Schiff碱（LIN804）的抑制率较高，都大于90%；N-（4-硝基苯甲酰基）-脱氢枞胺（2d）、N-（4-硝基苯甲酰基）-12-硝基脱氢枞胺（3d）、12，14-二硝基脱氢枞胺-吲哚-3-甲醛Schiff碱（LIN608）以及4-羟基-水杨醛缩12-氨基乙酰脱氢枞胺Schiff碱（LIN702）的抑制率在80~90%之间。
（11）采用滤纸片法测定了脱氢枞胺衍生物的抗菌活性，结果表明，N-（4-氯苯甲酰基）-脱氢枞胺-7-酮（4b）、N-（4-硝基苯甲酰基）-脱氢枞胺-7-酮（4d）和N-（4-氯苯甲酰基）-脱氢枞胺-7-肟（5b）对金黄色葡萄球菌、化合物5b对枯草芽孢杆菌、化合物4b和5b对大肠杆菌有较强的抑制作用。
（12）将25个脱氢枞胺衍生物对卵巢癌细胞株Hey-1B的半数抑制浓度（IC50，μmol/L）作为对象，对其进行2D-QSAR研究，以预测如何对化合物进行结构改造可增加其抗癌活性。结果表明，增加化合物的脂溶性、或增加芳香环结构、或增加化合物的折射率均有利于增加化合物的抗卵巢癌Hey-1B活性。
（13）采用饱和溶液法制备了脱氢枞胺（4-羟基）水杨醛Schiff碱β-环糊精包合物，采用红外光谱、差示扫描量热法（DSC）以及紫外光谱对包合物进行鉴定。研究了脱氢枞胺（4-羟基）水杨醛Schiff碱和其包合物的抗癌活性。结果表明：脱氢枞胺（4-羟基）水杨醛Schiff碱和环糊精可形成摩尔比为1：1的包合物；β-环糊精可以提高脱氢枞胺（4-羟基）水杨醛Schiff碱在混合溶剂（DMSO/H_2O=1/1，体积比）中的溶解度，増溶倍数为3.4；在浓度为10μg/mL时，脱氢枞胺（4-羟基）水杨醛Schiff碱和其包合物对卵巢癌细胞株Hey-1B的抑制率分别达到50.34%和41.65%。
Rosin is a mixture of various resin acids, small quantity of fatty acids and neutral substances.The main components of rosin are resin acids, which account to over90%of the total. Rosin isan important forestry resource of our country, and the output occupies the first place in the world.Deep-processing products of rosin were used not only in traditional industrial areas such aspapermaking, painting, soap, printing ink, but also in biomedicine field.
Dehydroabietylamine which has three-ring phenanthrene skeleton in molecule is one ofimportant modified products of rosin, and it is also main components of disproportionated rosinamine. In this paper, a series of amide derivatives was synthesized through reaction ofdehydroabietylamine and (substituted) benzoyl chlorides. Functional groups such as carbonylgroup, nitro group, oximido group, hydroxyl group, etc. were introduced on B ring and C ringthrough oxidation, nitration, oximation and reduction. Carboxymethyl was introduced intodehydroabietylamine by modification of amino group. The novel dehydroabietylaminederivatives were characterized by IR,1H NMR,13C NMR, MS, and HRMS. Anticancer activities,androgen receptor(AR) binding activities, blocking/agitating activities to α1A-adrenoceptor,inhibitory activities on Cdc25B phosphatase, inhibitory activities against KDR and antibacterialactivities of dehydroabietylamine derivatives were tested. The structure-activity relationship werestudied and summarized. Dehydroabietylamine4-hydroxysalicylidene Schiff base complexesenwrapped with β-cyclodextrin were prepared by saturation solution method. Structure andanticancer activity of the inclusion complexes were studied. Through induction-arrangement ofdata, the conclusions were drawn as followings:
(1) Dehydroabietylamine was purified by salt forming method, through reaction ofdisproportionated rosin amine and p-toluene sulphonic acid with yield of63.7%. Analogues ofN-benzoyl-dehydroabietylamine (2a~2d) were synthesized through reaction ofdehydroabietylamine and (substituted) benzoyl chlorides with yield of68.4~72.8%.
(2) Nitro group was introduced in the12th position and analogues of N-benzoyl-12-nitrodehydroabietylamine (3a~3d) were obtained through nitration on ring C ofdehydroabietylamine derivatives using copper nitrate-acetic anhydride system with yield of69.6~74.8%. Copper nitrate-acetic anhydride system used in this experiment has characteristicsof moderate reaction and good selectivity, compared with the traditional HNO_3-H_2SO_4mixedacid system.
(3) Chromic anhydride absorbed on100~200mesh macroporous silicon gel was prepared asa CrO_3/SiO_2solid-supported oxidizing reagent. Synthesis of N-benzoyl-dehydroabietylamine-7-one (4a) via selective oxidation of N-benzoyl-dehydroabietylamine (2a) by CrO_3/SiO_2solid-supported oxidizing reagent was studied. Effect of solvent species, solvent quantity,reaction temperature, loading amount and oxidant dosage on the yield was investigated. Experimental results indicated that analogues of N-benzoyl-dehydroabietylamine-7-one(4a~4e) can be obtained with yield of53.0~60.2%through introduction of carbonyl group in the7th position of ring B by oxidation of2.57mmol analogues of N-benzoyl-dehydroabietylamine(2a~2d,3a) in the present of2equimolar amount of CrO_3/SiO_2(loading amount2.0mmol/g) in50mL cyclohexane under the reflux temperature for8h. Compared with the traditionalCrO_3/CH3COOH liquid system, post-treatment process of products is more simple usingCrO_3/SiO_2solid-supported oxidizing reagent. It has a certain significance in environmentalprotection that these is not production of chromium waste liquid during the preparation ofCrO_3/SiO_2solid-supported oxidizing reagent and separation and purification of products.
(4) Analogues of N-benzoyl-dehydroabietylamine-7-oxime (5a~5d) were obtainedthrough oximation of carbonyl group in the7th position of ring B using hydroxylaminehydrochloride with yield of80.6~85.3%. N-benzoyl-dehydroabietylamine-7-ol (6a) and N-(2-chlorobenzoyl)-dehydroabietylamine-7-ol (6c) were obtained through reduction of carbonylgroup in the7th position of ring B using sodium borohydride with yield of84.3%and83.2%respectively..
(5) N, N-dicarboxymethyl dehydroabietylamine (7) and N-carboxymethyldehydroabietylamine (potassium salt)(8) were obtained with yield of58.3%and53.0%respectively under alkaline conditions, using dehydroabietylamine and chloroacetic acid as rawmaterials. Regulation of pH value is the key technique in this experiment.
(6) Antitumor activities of dehydroabietylamine derivatives (2a,2c,2d,3a,3c,3d,4a,4cand4d) against PC-3(human prostate carcinoma cell line) and Hey-1B (human ovariancarcinoma cell line) cells by the MTT assay were investigated. IC50values of compounds onPC-3and Hey-1B cell lines were5.7~84.9μg/mL and11.3~129.8μg/mL respectively. The7thposition on ring B and the12th position on ring C of dehydroabietylamine derivatives might bevery important active sites, which have great influence on antitumor activities by structureactivity relationship study. Antitumor activities of some compounds against PC-3and Hey-1Bcell lines were enhanced through the introduction of carbonyl group in the7th position of ring Band nitro group in the12th position of ring C. For instance, IC50values on PC-3and Hey-1B ofN-benzoyl-dehydroabietylamine-7-one (4a) which has a carbonyl group in the7th position onring B are only9.1%and26.0%of its parent compound N-benzoyl-dehydroabietylamine (2a).IC50values on PC-3and Hey-1B of N-benzoyl-12-nitrodehydroabietylamine (3a) which has anitro group in the12th position on ring C are only13.1%and18.3%of its parent compound2a.
(7) Cytotoxicity of some dehydroabietylamine derivatives against HepG2(humanhepatocarcinoma cell line) and L02(human hepatocyte cell line) cells were tested by the MTTassay. The results showed that, N-(4-nitrobenzoyl)-12-nitrodehydroabietylamine (3d) and N-benzoyl-dehydroabietylamine-7-one (4a) show high cytotoxicity on HepG2cells, but show lowcytotoxicity on L02.
(8) Androgen receptor (AR) binding activities of dehydroabietylamine derivatives weretested by ligand-receptor competitive binding assay in vitro. It has been found that N-benzoyl-dehydroabietylamine-7-one (4a) present a certain binding activity with AR with IC50value of83.8nmol/L at an initial concentration of10μmol/L.
(9) Blocking/agitating activities to α1A-adrenoceptor of compounds were tested usingCalcium mobilization assays. The results showed that N-benzoyl-dehydroabietylamine-7-oxime (5a) has25%antagonistic effect on α1A-adrenoceptor, and N-(2-chlorobenzoyl)-dehydroabietylamine-7-one (4c), N-(4-nitrobenzoyl)-dehydroabietylamine-7-one (4d) andN-benzoyl-12-nitrodehydroabietylamine-7-one (4e) have45~50%antagonistic effect onα1A-adrenoceptor at the concentration of10μmol/L.
(10) Inhibitory activity of compounds against kinase insert domain containing receptor(KDR) was studied using homogeneous time resolved fluorescence (HTRF) technology. It hasbeen found that the tested compounds present a certain inhibitory activity against KDR with theinhibition rates of38.27~99.34%at the concentration of4×10-4mol/L. Among these compounds,N-benzoyl-dehydroabietylamine-7-one (4a), N-(4-nitrobenzoyl)-dehydroabietylamine-7-one (4d), dehydroabietylamine3,4-dihydroxy-salicylidene Schiff base (LIN110), N-(2-hydroxy)-benzyl-dehydroabietylamine hydrochloride (LIN402), N-(5-nitro-2-hydroxy)-benzyl-dehydroabietylamine hydrochloride (LIN404),12,14-dinitro dehydroabietylamine4-hydroxy-benzaldehyde Schiff base (LIN609) and12-nitro-dehydroabietylamine5-nitro-salicylaldehyde Schiff base (LIN804) show relatively high inhibition rates that are more than90%. The inhibition rates of N-(4-nitrobenzoyl)-dehydroabietylamine (2d), N-(4-nitrobenzoyl)-12-nitrodehydroabietylamine (3d),12,14-dinitro dehydroabietylamine-indole-3-carboxaldehyde Schiff base (LIN608) and4-hydroxy-salicylidene-12-amino-acetyl-dehydroabietylamine Schiff base (LIN702) were80~90%.
(11) Antibacterial activities of dehydroabietylamine derivatives were studied by filter papermethod. The results showed that N-(4-chlorobenzoyl)-dehydroabietylamine-7-one (4b), N-(4-nitrobenzoyl)-dehydroabietylamine-7-one (4d) and N-(4-chlorobenzoyl)-dehydroabietylamine-7-oxime (5b) have strong inhibition effect on the growth ofStaphylococcus aureus, compound5b has strong inhibition effect on the growth of Bacillussubtilis, compound4b and5b have strong inhibition effect on the growth of Escherichia coli.
(12)2D-QSAR was studied using IC50values of25dehydroabietylamine derivatives onHey-1B in order to predict the structure reformation method for high antitumor activity. Theresults showed that increase of lipid solubility, aromatic ring structure or refractive index ofcompounds were beneficial to activity enhancement of compounds against Hey-1B cells.
(13) Dehydroabietylamine4-hydroxy-salicylidene Schiff base complexes enwrapped withβ-cyclodextrin were prepared by saturation solution method. The inclusion complexes wereidentified by infrared spectrum, differential scanning calorimetry (DSC) and ultraviolet spectrum.The antitumor activities of the dehydroabietylamine4-hydroxy-salicylidene Schiff base and the inclusion complexes were studied. The results showed that, An1:1molar ratiodehydroabietylamine4-hydroxy-salicylidene Schiff base complexes enwrapped withβ-cyclodextrin could be formed. The solubility of dehydroabietylamine4-hydroxy-salicylideneSchiff base in mixture solvent (DMSO/H_2O=1/1, volume ratio) was increased in3.4folds bythe formation of inclusion complex with β-cyclodextrin. The inhibitory ratio of thedehydroabietylamine4-hydroxy-salicylidene Schiff base and the inclusion complexes onHey-1B (human ovarian carcinoma cell line) were50.34%and41.65%at the concentration of10μg/mL.
引文
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