黄体酮系列衍生物的合成及生物活性研究
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摘要
甾体衍生物通常呈现出多样的生物活性，因此近年来针对甾体分子结构的合理修饰被广泛研究。实验表明：甾类苯亚甲基衍生物具有抗菌、抗肿瘤等生物活性；而在甾体结构的A-环或者D-环引入含N、O、S等杂原子的杂环时其相应的甾体衍生物将产生抗炎、降低胆固醇和利尿等活性。黄体酮是孕甾烷系列中一种最重要的孕激素，对于维持性周期和妊娠起着重要的作用，被视为激素特别是雌激素的平衡器，其结构为孕甾-4-烯-3,20-二酮。科学研究表明，由黄体酮衍生而来的化合物具有广泛的生物活性，例如在治疗外伤性脑损伤中的神经保护作用以及潜在的抗炎和抗菌等活性。
基于黄体酮对人体的重要性及其固有的甾体骨架，本文在前人针对甾体结构进行合理修饰的基础上，以黄体酮为原料，合成了多个系列的衍生物（主要合成路线见图1），共81个化合物，其中包括71个新化合物。主要研究结果如下：
1.以黄体酮（1）为起始原料，通过1,2-位脱氢生成孕甾-1,4-二烯-3,20-二酮（2）；在黄体酮（1）的4-位引入氯原子得4-氯孕甾-4-烯-3,20-二酮（4），后者经1,2-位脱氢转化为另一个中间产物4-氯孕甾-1,4-烯-3,20-二酮（5）。以化合物2和5为底物，使之分别与芳香醛6a-h发生羟醛缩合反应生成相应的苯亚甲基衍生物7a-h和8a-h，评价了此类化合物对海虾幼虫（Artemia salina）致死活性及抑制小鼠肺癌细胞（LLC）增殖的活性。
结果显示：化合物7a-h有相似的致死海虾活性（LC_(50)介于17.7-28.3μg/mL之间），而分子结构中具有相同芳香基片段、且4-位含一个氯原子的系列化合物8a-h却没有此类活性（LC50﹥50μg/mL）。MTT法测定细胞毒活性结果表明，苯亚甲基衍生物7a-h和8a-h在浓度为30μg/mL时，对LLC细胞有一定的抑制活性（抑制率介于5.96%-66.18%之间），其中7f和8a的活性较强，抑制率分别为66.18%和51.12%。
2.将苯亚甲基化合物7g中苯环上4′-NO_2还原得到4′-NH_2衍生物9，9分别与酰氯10a-v发生酰化反应生成相应的4′-酰胺基取代的苯亚甲基衍生物11a-v，评价了此类衍生物对海虾幼虫（Artemia salina）致死活性及抑制人体宫颈癌细胞（HeLa）和乳腺癌细胞（MCF-7）增殖的活性。
结果显示：4′-NO_2还原为-NH_2后有助于致死海虾活性提高（7g和9的LC50值分别为27.6μg/mL和15.9μg/mL）；但当4′-NH_2发生酰化反应后所得的4′-酰胺基修饰的苯亚甲基衍生物11a-v其相应的致死海虾活性明显减弱甚至消失。MTT法测定细胞毒活性结果表明，苯亚甲基衍生物11a-v在浓度为30μg/mL时，对HeLa和MCF-7细胞均有一定的抑制活性（HeLa细胞的抑制率介于21.83%-58.13%，MCF-7细胞的抑制率介于1.19%-64.00%），且11a-v中苯环上4′-取代酰胺基的变化显著影响其相应的癌细胞抑制活性。
其中，11f对HeLa和MCF-7两种癌细胞的抑制活性最强，抑制率分别为58.13%和64.00%。
3.以苯亚甲基衍生物7a-h和8a-h为起始反应物，通过在醋酸溶液中和水合肼的关环反应得到了C17-吡唑啉基衍生物12a-h和13a-h，考察了此类化合物对海虾幼虫（Artemiasalina）致死活性及抑制人体肺癌细胞（NCI-H460）、宫颈癌细胞（HeLa）和肝癌细胞（HepG2）增殖的活性，并进一步评价了高活性的吡唑啉基衍生物13b的细胞周期干预情况，应用流式细胞术测定了不同浓度化合物13b（10μg/mL、20μg/mL及40μg/mL）对HeLa细胞周期分布的影响。此外，采用浸叶法考察了13a-h对4龄粘虫（Mythimnaseparata）的毒杀活性。
结果显示：12a-h有较强的致死海虾活性（LC_(50)值介于18.94-44.89μg/mL之间），而分子结构中具有相同芳香基片段、且4-位含有一个氯原子的吡唑啉基衍生物13a-h具有更强的此类活性（LC_(50)值介于4.99-27.33μg/mL之间），其中13a的活性最好（LC_(50)=4.99μg/mL）。MTT法测定细胞毒活性结果表明，吡唑啉基衍生物13a-e对三种人体癌细胞（NCI-H460、HeLa和HepG2）均具有较好的抑制活性（IC_(50)值介于10.3-26.6μg/mL之间）。HeLa细胞周期实验结果表明，化合物13b使HeLa细胞阻滞在了S期，且S期DNA含量与浓度呈依赖关系，这一结果表明13b抑制细胞增殖与其诱导细胞周期停滞有关。
实验表明13a-h有不同程度的毒杀4龄粘虫（Mythimna separata）的活性，其中苯环上没有任何取代基的吡唑啉基衍生物13a的活性最好，其半数致死量LD50为296.65μg/g，接近阳性对照药剂苦皮藤素V的半数致死剂量（LD_(50)=260.05μg/g）。
4.黄体酮（1）4-位引入羟基生成4-羟基黄体酮（14），后者和酰氯15a-p反应生成相应的4-酰氧基黄体酮衍生物16a-p，它们的相关活性正在探索之中
5.此外，对合成黄体酮噻唑类衍生物进行了实验尝试。
There has been an extensive research towards the rational modification of steroidmolecules probably because of the various advantages associated with steroidal derivatives. Ithas been proved by different ring modification studies of steroidal molecules involving the A-and D-ring whereby incorporation of heteroatom (N, O or S) has been reported to show awide range of different biological activities such as anti-inflammatory, hypocholesterolemicand diuretic activities. Progesterone is one of the most important hormones of the steroidalpregnane series and plays important roles for the maintenance of sexual cycle and pregnancyand can be regarded as a hormonal balancer, particularly of estrogens. The structure ofprogesterone is pregn-4-ene-3,20-dione and a large number of studies revealed thatderivatives of progesterone have varied biological activities, such as remarkableneuroprotection following traumatic brain injury as well as potential antimicrobial andanti-inflammatory functions.
Due to the importance of progesterone to the human body and its inherent steroidalstructure, based on previous work on rational modification of steroid molecules, wesynthesized a few series compounds derived from progesterone (The synthetic route are listedin figure1). Eighty-one compounds were obtained, of which seventy-one compounds werethe first time to report. The results are concluded as follow:
1.Pregn-1,4-diene-3,20-dione2was directly obtained through1-dehydrogenation ofprogesterone1. On the other hand, introduction of a chlorine atom at C-4of1and then1-dehydrogenation gave another intermediate,4-chloro-pregn-diene-3,20-dione5. Then, aldolcondensation reactions of the intermediates2and5with various benzaldehydes6a-h,afforded the corresponding target benzylidene derivatives7a-h and8a-h. These compoundswere evaluated for their cytotoxic activty against brine shrimp (Artemia salina) and murineLewis lung carcinoma cells (LLC).
It was found that these compounds7a-hexhibited similar cytotoxicity against brineshrimp, with LC50values of17.7-28.3μg/mL.In contrast, compounds8a-h, which contained achlorine atom at C-4position and possessed the same counterpart of aromatic aldehydes as7a-h, caused a loss of activity (LC_(50)>50μg/mL). From the cytotoxicity results tested by the
MTT assay, we found that the benzylidene derivatives7a-h and8a-h showed someinhibitive effects (inhibition rate of5.96%to66.18%) to LLC cells at concentrations of30μg/mL, of which7f and8a displayed a weak cytotoxic activity (66.18%and51.12%,respectively) at this concentration.
2.4′-Nitro of benzylidene derivative7g was reduced to afford4′-amino and obtainedcompound9. Then,9underwent aminoacylation with acyl chloride10a-v to provide thetarget4′-acylamino-modified benzylidene derivatives11a-v. These compounds wereevaluated for their cytotoxic activty against brine shrimp (Artemia salina) and two humancancer cell lines i (HeLa and MCF-7).
It was found that after4′-nitro compound7g was reducted to4′-amino derivative9, thecorresponding cytotoxicity against brine shrimp was enhanced with the LC50value changedfrom27.6μg/mL to15.9μg/mL. In contrast, all of the4′-acylaminobenzylidene derivatives11a-v displayed weaker or even disappeared such activity. From the cytotoxicity results testedby the MTT assay, we found that the benzylidene derivatives11a-v at concentrations of30μg/mL showed some inhibitive effects and and the variation of acylamino groups at4′-position on the benzene ring were sensitive to the cytotoxic activity response. Theinhibition rate of two cells (HeLa and MCF-7) were ranged form21.83%to66.18%and1.19%to64.00%, respectively, of which, compound11f exhibited the strongest inhibitoryeffects on both cell lines (58.13%of HeLa and64.00%of MCF-7) at at this concentration.
3.Through cyclisation reaction with hydrazine hydrate in acetic acid solution, substrate7a-h and8a-h further offered C-17pyrazolinyl derivatives12a-h and13a-h. Thesecompounds were evaluated for their cytotoxic activty against brine shrimp (Artemia salina)and three human cancer cell lines (NCI-H460, HeLa and HepG2). The effects on cell cycledistribution of HeLa cells which treated with different concentrations of the most potentpyrazolinyl compound13b (10,20or40μg/mL) were evaluated by flow cytometry.Moreover, we measured the insecticidal activities against the4~(th) instar larvae (Mythimnaseparata) of13a-h by the leaf disc method.
The results indicated that compounds13a-h significantly inhibited the growth of thebrine shrimp larvae (LC_(50)=4.99-27.33μg/mL), of which, compound13a was the most activeone ((LC_(50)=4.99μg/mL). On the other hand, compounds12a-h, which lacked a chlorineatom at C-4position and possessed the same counterpart of aromatic aldehydes as13a-h,caused a decrease in activity (LC_(50)=18.94-44.89μg/mL). From the cytotoxicity resultstested by the MTT assay, we found that the pyrazolinyl13a-e exhibited moderate in vitrocytotoxic activity to the three human cancer cell lines (NCI-H460, HeLa and HepG2),showing IC50values ranging from10.3to26.6μg/mL. The HeLa cell cycle distributionanalysis indicated that13b arrested the cell population in the S phase and its concentrationsaffected the DNA percentage of S phase. This results imply that the cytotoxic effect of13bcould be preceded by the accumulation of cells in the S phase.
It was also found that13a-h showed potent insecticidal activity against the4thinstarlarvae of M. separata. Notably, compounds7a, with a none substituent aromatic ring, wasfound to exert the most potent insecticidal activity (LD_(50)=296.65μg/g), comparable to thatof the positive control celangulatin V (LD_(50)=260.05μg/g).
4.4-Hydroxyprogesterone (14) was obtained by introduction of a hydroxy at C-4ofprogesterone1.Then,14reacted with acyl chloride15a-p to offer4-acyloxyprogesterone derivatives16a-p. Their relative bioactivity are under investigation.
5.In additional, an attempt to synthesize the thiazole derivatives from progesterone wasdone.
基于黄体酮对人体的重要性及其固有的甾体骨架，本文在前人针对甾体结构进行合理修饰的基础上，以黄体酮为原料，合成了多个系列的衍生物（主要合成路线见图1），共81个化合物，其中包括71个新化合物。主要研究结果如下：
1.以黄体酮（1）为起始原料，通过1,2-位脱氢生成孕甾-1,4-二烯-3,20-二酮（2）；在黄体酮（1）的4-位引入氯原子得4-氯孕甾-4-烯-3,20-二酮（4），后者经1,2-位脱氢转化为另一个中间产物4-氯孕甾-1,4-烯-3,20-二酮（5）。以化合物2和5为底物，使之分别与芳香醛6a-h发生羟醛缩合反应生成相应的苯亚甲基衍生物7a-h和8a-h，评价了此类化合物对海虾幼虫（Artemia salina）致死活性及抑制小鼠肺癌细胞（LLC）增殖的活性。
结果显示：化合物7a-h有相似的致死海虾活性（LC_(50)介于17.7-28.3μg/mL之间），而分子结构中具有相同芳香基片段、且4-位含一个氯原子的系列化合物8a-h却没有此类活性（LC50﹥50μg/mL）。MTT法测定细胞毒活性结果表明，苯亚甲基衍生物7a-h和8a-h在浓度为30μg/mL时，对LLC细胞有一定的抑制活性（抑制率介于5.96%-66.18%之间），其中7f和8a的活性较强，抑制率分别为66.18%和51.12%。
2.将苯亚甲基化合物7g中苯环上4′-NO_2还原得到4′-NH_2衍生物9，9分别与酰氯10a-v发生酰化反应生成相应的4′-酰胺基取代的苯亚甲基衍生物11a-v，评价了此类衍生物对海虾幼虫（Artemia salina）致死活性及抑制人体宫颈癌细胞（HeLa）和乳腺癌细胞（MCF-7）增殖的活性。
结果显示：4′-NO_2还原为-NH_2后有助于致死海虾活性提高（7g和9的LC50值分别为27.6μg/mL和15.9μg/mL）；但当4′-NH_2发生酰化反应后所得的4′-酰胺基修饰的苯亚甲基衍生物11a-v其相应的致死海虾活性明显减弱甚至消失。MTT法测定细胞毒活性结果表明，苯亚甲基衍生物11a-v在浓度为30μg/mL时，对HeLa和MCF-7细胞均有一定的抑制活性（HeLa细胞的抑制率介于21.83%-58.13%，MCF-7细胞的抑制率介于1.19%-64.00%），且11a-v中苯环上4′-取代酰胺基的变化显著影响其相应的癌细胞抑制活性。
其中，11f对HeLa和MCF-7两种癌细胞的抑制活性最强，抑制率分别为58.13%和64.00%。
3.以苯亚甲基衍生物7a-h和8a-h为起始反应物，通过在醋酸溶液中和水合肼的关环反应得到了C17-吡唑啉基衍生物12a-h和13a-h，考察了此类化合物对海虾幼虫（Artemiasalina）致死活性及抑制人体肺癌细胞（NCI-H460）、宫颈癌细胞（HeLa）和肝癌细胞（HepG2）增殖的活性，并进一步评价了高活性的吡唑啉基衍生物13b的细胞周期干预情况，应用流式细胞术测定了不同浓度化合物13b（10μg/mL、20μg/mL及40μg/mL）对HeLa细胞周期分布的影响。此外，采用浸叶法考察了13a-h对4龄粘虫（Mythimnaseparata）的毒杀活性。
结果显示：12a-h有较强的致死海虾活性（LC_(50)值介于18.94-44.89μg/mL之间），而分子结构中具有相同芳香基片段、且4-位含有一个氯原子的吡唑啉基衍生物13a-h具有更强的此类活性（LC_(50)值介于4.99-27.33μg/mL之间），其中13a的活性最好（LC_(50)=4.99μg/mL）。MTT法测定细胞毒活性结果表明，吡唑啉基衍生物13a-e对三种人体癌细胞（NCI-H460、HeLa和HepG2）均具有较好的抑制活性（IC_(50)值介于10.3-26.6μg/mL之间）。HeLa细胞周期实验结果表明，化合物13b使HeLa细胞阻滞在了S期，且S期DNA含量与浓度呈依赖关系，这一结果表明13b抑制细胞增殖与其诱导细胞周期停滞有关。
实验表明13a-h有不同程度的毒杀4龄粘虫（Mythimna separata）的活性，其中苯环上没有任何取代基的吡唑啉基衍生物13a的活性最好，其半数致死量LD50为296.65μg/g，接近阳性对照药剂苦皮藤素V的半数致死剂量（LD_(50)=260.05μg/g）。
4.黄体酮（1）4-位引入羟基生成4-羟基黄体酮（14），后者和酰氯15a-p反应生成相应的4-酰氧基黄体酮衍生物16a-p，它们的相关活性正在探索之中
5.此外，对合成黄体酮噻唑类衍生物进行了实验尝试。
There has been an extensive research towards the rational modification of steroidmolecules probably because of the various advantages associated with steroidal derivatives. Ithas been proved by different ring modification studies of steroidal molecules involving the A-and D-ring whereby incorporation of heteroatom (N, O or S) has been reported to show awide range of different biological activities such as anti-inflammatory, hypocholesterolemicand diuretic activities. Progesterone is one of the most important hormones of the steroidalpregnane series and plays important roles for the maintenance of sexual cycle and pregnancyand can be regarded as a hormonal balancer, particularly of estrogens. The structure ofprogesterone is pregn-4-ene-3,20-dione and a large number of studies revealed thatderivatives of progesterone have varied biological activities, such as remarkableneuroprotection following traumatic brain injury as well as potential antimicrobial andanti-inflammatory functions.
Due to the importance of progesterone to the human body and its inherent steroidalstructure, based on previous work on rational modification of steroid molecules, wesynthesized a few series compounds derived from progesterone (The synthetic route are listedin figure1). Eighty-one compounds were obtained, of which seventy-one compounds werethe first time to report. The results are concluded as follow:
1.Pregn-1,4-diene-3,20-dione2was directly obtained through1-dehydrogenation ofprogesterone1. On the other hand, introduction of a chlorine atom at C-4of1and then1-dehydrogenation gave another intermediate,4-chloro-pregn-diene-3,20-dione5. Then, aldolcondensation reactions of the intermediates2and5with various benzaldehydes6a-h,afforded the corresponding target benzylidene derivatives7a-h and8a-h. These compoundswere evaluated for their cytotoxic activty against brine shrimp (Artemia salina) and murineLewis lung carcinoma cells (LLC).
It was found that these compounds7a-hexhibited similar cytotoxicity against brineshrimp, with LC50values of17.7-28.3μg/mL.In contrast, compounds8a-h, which contained achlorine atom at C-4position and possessed the same counterpart of aromatic aldehydes as7a-h, caused a loss of activity (LC_(50)>50μg/mL). From the cytotoxicity results tested by the
MTT assay, we found that the benzylidene derivatives7a-h and8a-h showed someinhibitive effects (inhibition rate of5.96%to66.18%) to LLC cells at concentrations of30μg/mL, of which7f and8a displayed a weak cytotoxic activity (66.18%and51.12%,respectively) at this concentration.
2.4′-Nitro of benzylidene derivative7g was reduced to afford4′-amino and obtainedcompound9. Then,9underwent aminoacylation with acyl chloride10a-v to provide thetarget4′-acylamino-modified benzylidene derivatives11a-v. These compounds wereevaluated for their cytotoxic activty against brine shrimp (Artemia salina) and two humancancer cell lines i (HeLa and MCF-7).
It was found that after4′-nitro compound7g was reducted to4′-amino derivative9, thecorresponding cytotoxicity against brine shrimp was enhanced with the LC50value changedfrom27.6μg/mL to15.9μg/mL. In contrast, all of the4′-acylaminobenzylidene derivatives11a-v displayed weaker or even disappeared such activity. From the cytotoxicity results testedby the MTT assay, we found that the benzylidene derivatives11a-v at concentrations of30μg/mL showed some inhibitive effects and and the variation of acylamino groups at4′-position on the benzene ring were sensitive to the cytotoxic activity response. Theinhibition rate of two cells (HeLa and MCF-7) were ranged form21.83%to66.18%and1.19%to64.00%, respectively, of which, compound11f exhibited the strongest inhibitoryeffects on both cell lines (58.13%of HeLa and64.00%of MCF-7) at at this concentration.
3.Through cyclisation reaction with hydrazine hydrate in acetic acid solution, substrate7a-h and8a-h further offered C-17pyrazolinyl derivatives12a-h and13a-h. Thesecompounds were evaluated for their cytotoxic activty against brine shrimp (Artemia salina)and three human cancer cell lines (NCI-H460, HeLa and HepG2). The effects on cell cycledistribution of HeLa cells which treated with different concentrations of the most potentpyrazolinyl compound13b (10,20or40μg/mL) were evaluated by flow cytometry.Moreover, we measured the insecticidal activities against the4~(th) instar larvae (Mythimnaseparata) of13a-h by the leaf disc method.
The results indicated that compounds13a-h significantly inhibited the growth of thebrine shrimp larvae (LC_(50)=4.99-27.33μg/mL), of which, compound13a was the most activeone ((LC_(50)=4.99μg/mL). On the other hand, compounds12a-h, which lacked a chlorineatom at C-4position and possessed the same counterpart of aromatic aldehydes as13a-h,caused a decrease in activity (LC_(50)=18.94-44.89μg/mL). From the cytotoxicity resultstested by the MTT assay, we found that the pyrazolinyl13a-e exhibited moderate in vitrocytotoxic activity to the three human cancer cell lines (NCI-H460, HeLa and HepG2),showing IC50values ranging from10.3to26.6μg/mL. The HeLa cell cycle distributionanalysis indicated that13b arrested the cell population in the S phase and its concentrationsaffected the DNA percentage of S phase. This results imply that the cytotoxic effect of13bcould be preceded by the accumulation of cells in the S phase.
It was also found that13a-h showed potent insecticidal activity against the4thinstarlarvae of M. separata. Notably, compounds7a, with a none substituent aromatic ring, wasfound to exert the most potent insecticidal activity (LD_(50)=296.65μg/g), comparable to thatof the positive control celangulatin V (LD_(50)=260.05μg/g).
4.4-Hydroxyprogesterone (14) was obtained by introduction of a hydroxy at C-4ofprogesterone1.Then,14reacted with acyl chloride15a-p to offer4-acyloxyprogesterone derivatives16a-p. Their relative bioactivity are under investigation.
5.In additional, an attempt to synthesize the thiazole derivatives from progesterone wasdone.
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