新型双噻吩并嘧啶酮衍生物的合成与性质
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摘要
噻吩并嘧啶酮衍生物具有广泛的生物活性，已成为农用化学品研究和开发的热点之一，其中一些已被开发用作杀虫剂、杀菌剂和医药。另一方面，双噻吩衍生物具有抗肿瘤、抗病毒等活性，并可用作抗生素、止痛和退热药，特别是其中一些还可用作有机导电材料。尽管噻吩并嘧啶酮类衍生物的研究异常活跃，但有关双噻吩并嘧啶酮类衍生物的研究文献报道极少。本文研究了利用aza-Wittig反应来合成双噻吩并嘧啶酮衍生物。具体研究内容如下：
1．合成了136个新型的双噻吩并嘧啶酮，6个新型杂环体系化合——5H-2,3-二硫杂-5,7-二氮杂环戊二烯并[cd]茚和10个未见文献报道过的中间体化合物。所有这些化合物都进行了IR，~1H NMR，EI-MS和元素分析，部分化合物还做了~(13)C NMR，对其中三个化合物进行了X-Ray单品衍射分析，进一步确认了化合物的结构。这些化合物是：
(1)双噻吩并单嘧啶酮(81个)
(2)双噻吩并双嘧啶二酮(55个)
(3)5H-2,3-二硫杂-5,7-二氮杂环戊二烯并[cd]茚(6个)
(4)中间体(10个)
2．由3,4-二氨基噻吩并[2，3-b]噻吩-2,5-二甲酸二乙酯选择性地合成了单膦亚胺1；从单膦亚胺1出发，运用aza-Wittig反应方法，合成了双噻吩并单嘧啶酮4，6，8；研究了单膦亚胺1和双噻吩并单嘧啶酮进一步制备膦亚胺的反应；改进了3,4-二氨基噻吩并[2，3-b]噻吩-2,5-二甲酸二乙酯的合成方法。
3．设计并合成了未见文献报道的3,6-二氨基噻吩并[3，2-b]噻吩-2,5-二甲酸二乙酯34，并由34制得了双膦亚胺24。从双膦亚胺24出发，运用aza-Wittig反应方法合成了双噻吩并双嘧啶酮二酮27，29，31，并研究了双膦亚胺24和芳基异氰酸酯反应的选择性。
4．研究了单膦亚胺1和芳基(或烷基)异氰酸酯作用生成的单碳二亚胺在碳酸钾的催化下自身关环，高产率地得到了未见文献报道过的5H-2,3-二硫杂-5,7-二氮杂环戊二烯并[cd]茚9。
5．设计并合成了双叠氮化合物17，从17出发，采用Staudinger反应方法合成了单、双膦亚胺18和15，并研究了双膦亚胺15和芳基异氰酸酯的反应。
6．研究了13个化合物的抗肿瘤活性，结果显示受试药物对人肺癌细胞A549具有显著的细胞毒作用，能抑制细胞的增殖，具有体外抗肿瘤活性。其中6h作用最强，在160μg·ml~(-1)浓度时具有与对照药丝裂霉素在80μg@ml~(-1)浓度时相当的抑制率(均为78．6％)，且具有明显的量效关系。8a的IC_(50)(药物的半数抑制溶度)低于10μg·ml~(-1)。
选取了20个化合物进行了抑菌活性测试，结果表明部分测试化合物具有较好的抑菌活性。如5a在100ppm浓度时对黄瓜灰霉菌的抑制率达到了84％。
The derivatives of thienopyrimidinones, one of the focuses in the research and development of agrochemicals, have been found to have widespread biological activities. Many of them have been used as pesticide, fungicide and medicine. On the other hand, the derivatives of bisthiophenes have been developed for different purposes in the pharmaceutical field and have been tested as potential antitumor, antiviral, antibiotic, analgesic and antipyretic drugs. Further more, some of them are of potential interest as organic electric materials. However, there is little report of a generally useful synthesis of bisthienopyrimidinones. In this paper, we studied the synthesis of novel bisthienopyrimidinones by utilizing aza-Wittig reaction. What the paper studied may be summarized as follows:
1.One hundred and thirty six novel bisthienopyrimidinones, six novel heterocyclic system of 5H-2,3-dithia-5,7-diaza-cyclopenta[cd]indenes and ten unreported intermediate were synthesized.The structure of all these compounds were confirmed by IR,~1H NMR, EI-MS and elementalanalyses. Some of them were confirmed by ~(13)C NMR and X-ray crystal diffraction.Thosecompounds are summarized as follows:
(1) bisthienomonopyrimidinones (81)
(2) bisthienobispyrimidindiones (55) (3) 5H-2,3-dithia-5,7-diaza-cyclopenta[cd]indenes (6)
(4) intermediates(10)
2.The selective synthesis of iminophosphorane 1 from diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate and further reaction of the isolated monoiminophosphorane 1 or bisthienomonopyrimidinones 4,6,8 with triphenylphosphine, hexachloroethane and triethylamine were studied. Novel bisthienomonopyrimidinones 4, 6, 8 were synthsizd from iminophosphorane 1 by utilizing aza-Wittig reaction. The method of preparation of diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate was studied and improved.
3.Novel diethyl 3,6-diaminothieno[3,2-b]thiophene-2,5-dicarboxylate 34 was designed and synthesized, and bisiminophosphorane 24 was easily prepared from 34. Bisthienobispyrimidindiones 27,29,31 were efficiently synthesized via aza-Wittig reactions from 24. The selective reactions of bisiminophosphorane 24 with aromatic isocyanates were also studied.
4. Monoiminophosphorane 1 reacted with aryl or alkyl isocyanates to give stable monocarbodiimides.However, in the presence of catalytic amount of potassium carbonate, the monocarbodiimides were transferred into previously unreported 5H-2,3-dithia-5,7-diaza-cyclopenta[cd]indenes 9 via direct cyclization in high yields.
5.Novel diazide 17 was designed and synthesized. Monoiminophosphorane 18 and bisiminophosphorane 15 were synthesized from bisazide 17 via Staudinger Reaction. The reactions of bisiminophosphorane 15 with aryl isocyanates were also studied.
6. The antitumor activities of 13 compounds were also researched and some of them displayed strongantiproliferative and cytotoxicity effect on human lung cancer cell lines A549. The best of them was 6h which displayed comparable inhibition (78.6%) in 160μg·ml~(-1) with standard Mitomycin (MMC) in 80μg·ml~(-1).The IC_(50) of 8a was less than 10μ·gm~(-1).
The antibacterial activities of 21 compounds were tested and some of them showed good fungicidal activities. For example, 5a exhibited 84% inhibition of Botrytis cinereapers in 100 ppm.
1．合成了136个新型的双噻吩并嘧啶酮，6个新型杂环体系化合——5H-2,3-二硫杂-5,7-二氮杂环戊二烯并[cd]茚和10个未见文献报道过的中间体化合物。所有这些化合物都进行了IR，~1H NMR，EI-MS和元素分析，部分化合物还做了~(13)C NMR，对其中三个化合物进行了X-Ray单品衍射分析，进一步确认了化合物的结构。这些化合物是：
(1)双噻吩并单嘧啶酮(81个)
(2)双噻吩并双嘧啶二酮(55个)
(3)5H-2,3-二硫杂-5,7-二氮杂环戊二烯并[cd]茚(6个)
(4)中间体(10个)
2．由3,4-二氨基噻吩并[2，3-b]噻吩-2,5-二甲酸二乙酯选择性地合成了单膦亚胺1；从单膦亚胺1出发，运用aza-Wittig反应方法，合成了双噻吩并单嘧啶酮4，6，8；研究了单膦亚胺1和双噻吩并单嘧啶酮进一步制备膦亚胺的反应；改进了3,4-二氨基噻吩并[2，3-b]噻吩-2,5-二甲酸二乙酯的合成方法。
3．设计并合成了未见文献报道的3,6-二氨基噻吩并[3，2-b]噻吩-2,5-二甲酸二乙酯34，并由34制得了双膦亚胺24。从双膦亚胺24出发，运用aza-Wittig反应方法合成了双噻吩并双嘧啶酮二酮27，29，31，并研究了双膦亚胺24和芳基异氰酸酯反应的选择性。
4．研究了单膦亚胺1和芳基(或烷基)异氰酸酯作用生成的单碳二亚胺在碳酸钾的催化下自身关环，高产率地得到了未见文献报道过的5H-2,3-二硫杂-5,7-二氮杂环戊二烯并[cd]茚9。
5．设计并合成了双叠氮化合物17，从17出发，采用Staudinger反应方法合成了单、双膦亚胺18和15，并研究了双膦亚胺15和芳基异氰酸酯的反应。
6．研究了13个化合物的抗肿瘤活性，结果显示受试药物对人肺癌细胞A549具有显著的细胞毒作用，能抑制细胞的增殖，具有体外抗肿瘤活性。其中6h作用最强，在160μg·ml~(-1)浓度时具有与对照药丝裂霉素在80μg@ml~(-1)浓度时相当的抑制率(均为78．6％)，且具有明显的量效关系。8a的IC_(50)(药物的半数抑制溶度)低于10μg·ml~(-1)。
选取了20个化合物进行了抑菌活性测试，结果表明部分测试化合物具有较好的抑菌活性。如5a在100ppm浓度时对黄瓜灰霉菌的抑制率达到了84％。
The derivatives of thienopyrimidinones, one of the focuses in the research and development of agrochemicals, have been found to have widespread biological activities. Many of them have been used as pesticide, fungicide and medicine. On the other hand, the derivatives of bisthiophenes have been developed for different purposes in the pharmaceutical field and have been tested as potential antitumor, antiviral, antibiotic, analgesic and antipyretic drugs. Further more, some of them are of potential interest as organic electric materials. However, there is little report of a generally useful synthesis of bisthienopyrimidinones. In this paper, we studied the synthesis of novel bisthienopyrimidinones by utilizing aza-Wittig reaction. What the paper studied may be summarized as follows:
1.One hundred and thirty six novel bisthienopyrimidinones, six novel heterocyclic system of 5H-2,3-dithia-5,7-diaza-cyclopenta[cd]indenes and ten unreported intermediate were synthesized.The structure of all these compounds were confirmed by IR,~1H NMR, EI-MS and elementalanalyses. Some of them were confirmed by ~(13)C NMR and X-ray crystal diffraction.Thosecompounds are summarized as follows:
(1) bisthienomonopyrimidinones (81)
(2) bisthienobispyrimidindiones (55) (3) 5H-2,3-dithia-5,7-diaza-cyclopenta[cd]indenes (6)
(4) intermediates(10)
2.The selective synthesis of iminophosphorane 1 from diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate and further reaction of the isolated monoiminophosphorane 1 or bisthienomonopyrimidinones 4,6,8 with triphenylphosphine, hexachloroethane and triethylamine were studied. Novel bisthienomonopyrimidinones 4, 6, 8 were synthsizd from iminophosphorane 1 by utilizing aza-Wittig reaction. The method of preparation of diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate was studied and improved.
3.Novel diethyl 3,6-diaminothieno[3,2-b]thiophene-2,5-dicarboxylate 34 was designed and synthesized, and bisiminophosphorane 24 was easily prepared from 34. Bisthienobispyrimidindiones 27,29,31 were efficiently synthesized via aza-Wittig reactions from 24. The selective reactions of bisiminophosphorane 24 with aromatic isocyanates were also studied.
4. Monoiminophosphorane 1 reacted with aryl or alkyl isocyanates to give stable monocarbodiimides.However, in the presence of catalytic amount of potassium carbonate, the monocarbodiimides were transferred into previously unreported 5H-2,3-dithia-5,7-diaza-cyclopenta[cd]indenes 9 via direct cyclization in high yields.
5.Novel diazide 17 was designed and synthesized. Monoiminophosphorane 18 and bisiminophosphorane 15 were synthesized from bisazide 17 via Staudinger Reaction. The reactions of bisiminophosphorane 15 with aryl isocyanates were also studied.
6. The antitumor activities of 13 compounds were also researched and some of them displayed strongantiproliferative and cytotoxicity effect on human lung cancer cell lines A549. The best of them was 6h which displayed comparable inhibition (78.6%) in 160μg·ml~(-1) with standard Mitomycin (MMC) in 80μg·ml~(-1).The IC_(50) of 8a was less than 10μ·gm~(-1).
The antibacterial activities of 21 compounds were tested and some of them showed good fungicidal activities. For example, 5a exhibited 84% inhibition of Botrytis cinereapers in 100 ppm.
引文
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