N-(安替比林-4-基)-N'-取代芳甲酰基硫脲的合成及其生物活性

合成了12个含安替比林基的取代芳甲酰基硫脲类化合物,用1H NMR,IR和元素分析确证了它们的结构,并进行了室内生物活性测试.生测实验证明部分酰基硫脲类化合物,比如N-(安替比林-4-基)-N'-m(或o)-甲苯甲酰基硫脲,N-(安替比林-4-基)-N-o-硝基苯甲酰基硫脲,N-(安替比林-4-基)-N'-m(或p)-氯苯甲酰基硫脲,具有一定的细胞分裂素活性.     

三嗪基苯硫甲基磺酰脲的合成

苯硫甲基磺酰胺(1)与4,6-二氯-2-三嗪异氰酸酯以碳酸钾为触媒在甲苯中加热回流制得N-4,6-二氯-2-三嗪基苯硫甲基磺酰脲(2),后者进一步与甲醇钠作用得N-4,6-二甲氧基-2-三嗪基苯硫甲基磺酰脲(3)。化合物3d经测试,具有一定的除草活性。     

新型含酰基脲桥和硫脲桥的苯双酰胺类似物的合成及生物活性

参考氟虫酰胺和除虫脲的活性结构片段,设计合成了一系列结构新颖的含有酰基脲桥和酰基硫脲桥的化合物,通过核磁共振氢谱、高分辨质谱以及X射线单晶衍射确定了其结构.生测结果表明,酰基脲桥和酰基硫脲桥结构的引入使杀虫活性降低,但是化合物7d在10 mg/L的浓度下,仍表现出一定的杀粘虫活性.此外发现部分化合物具有一定的抑菌活性,其中化合物8f对苹果轮纹、小麦纹枯和水稻恶苗病原菌的抑制率分别为75.0%、87.5%和84.6%.     

N-(4,6-二取代嘧啶-2-基)-N′-(1-甲基-3-乙基-4-氯吡唑-5-基)甲酰基(硫)脲的合成及生物活性

利用活性结构拼接原理,将高效杀螨剂吡螨胺分子的吡唑环部分引入酰基(硫)脲化合物中,以1-甲基-3-乙基-4-氯-5-甲酸基吡唑和2-氨基-4,6-二取代嘧啶为起始原料,通过多步反应合成了5种N-(4,6-二取代嘧啶-2-基)-N′-(1-甲基-3-乙基-4-氯吡唑-5-基)甲酰基脲和5个N-(4,6-二取代嘧啶-2-基)-N′-(1-甲基-3-乙基-4-氯吡唑-5-基)甲酰基硫脲化合物,其化合物结构经IR、1HNMR及元素分析测试技术确证。初步生物活性试验表明,在50mg/L质量浓度下目标化合物的杀螨活性不太理想,但有些化合物具有较好的除草活性,其中化合物Ⅰb、Ⅰc和Ⅰe对稗草主根的生长抑制率大于60%。     

N-(4,6-二取代嘧啶-2-基)-N'-(1-甲基-3-乙基-4-氯吡唑-5-基)甲酰基(硫)脲的合成及生物活性

利用活性结构拼接原理,将高效杀螨剂吡螨胺分子的吡唑环部分引入酰基（硫）脲化合物中,以1-甲基-3-乙基-4-氯-5-甲酸基吡唑和2-氨基-4,6-二取代嘧啶为起始原料,通过多步反应合成了5种N-（4,6-二取代嘧啶-2-基）-N’-（1-甲基-3-乙基-4-氯吡唑-5-基）甲酰基脲和5个N-（4,6-二取代嘧啶-2．基）-N’-（1．甲基-3-乙基-4-氯吡唑-5-基）甲酰基硫脲化合物,其化合物结构经IR、^1HNMR及元素分析测试技术确证。初步生物活性试验表明,在50mg／L质量浓度下目标化合物的杀螨活性不太理想,但有些化合物具有较好的除草活性,其中化合物Ib、Ic和Ie对稗草主根的生长抑制率大于60％。     

超声辐射法在新型含双杂环芳酰基硫脲合成中的应用

以2-苯基-1,2,3-三唑-4-甲酸、氨基硫脲为原料在三氯氧磷中反应得到2-氨基-5-(2-苯基-1,2,3-三唑-4-基)-1,3,4-噻二唑,然后分别采用超声辐射法和常规加热法与芳酰基异硫氰酸酯反应合成了一系列的N-[5-(2-苯基-1,2,3-三唑-4-基) 1,3,4-噻二唑-2-基\]-N′-酰基硫脲。 通过与常规方法比较,采用超声辐射法反应时间只有原来的12.5%,反应产率提高了4%~17%,减少了副反应。 所有化合物的结构经元素分析、MS、IR、1H NMR测试技术确证。     

N-取代苯基-N''''-(1-甲基-3-乙基-4-氯-5-吡唑甲酰基)(硫)脲的合成及其杀螨活性

利用活性结构拼接原理,将高效杀螨剂吡螨胺分子的吡唑环部分引入酰基(硫)脲化合物的分子中,合成了6个新的N-取代苯基-N'-(1-甲基-3-乙基-4-氯-5-吡唑甲酰基)脲(2a～2f)和6个新的N-取代苯基-N'-(1-甲基-3-乙基-4-氯-5-吡唑甲酰基)硫脲(3a～3f),收率44%～89%.2和3的结构经1H NMR,IR和元素分析表征.用叶片浸液法测定了2和3对红蜘蛛的毒杀作用,初步实验结果表明它们有一定的杀螨活性.     

新型N-(取代芳氧乙酰胺基)-N'-(1-甲基环己基酰基)硫脲及其环合产物的合成及其杀虫活性

采用亚结构拼接法,将苯氧乙酸类结构引入酰基硫脲中,设计并合成了8个新型的硫脲类化合物——N-(取代苯氧乙酰胺基)-N'-(1-甲基环己基酰基)硫脲(5a~5h);5a~5h在酸性条件下关环形成8个新型的含1,3,4-噻二唑的酰胺类化合物——1-甲基-N-(5-取代基-1,3,4-噻二唑-2-基)环氧甲酰胺(6a~6h),其结构经1H NMR和ESI-MS表征。初步的生物活性测试结果表明,在用药量为500mg·L-1时,N-(2,4-二氯苯氧乙酰胺基)-N'-(1-甲基环己基酰基)硫脲对粘虫的抑制率为80%。     

N-取代苯基-N′-（1-甲基-3-乙基-4-氯-5-吡唑甲酰基）（硫）脲的合成及其杀螨活性

利用活性结构拼接原理,将高效杀螨剂吡螨胺分子的吡唑环部分引入酰基(硫)脲化合物的分子中,合成了6个新的N-取代苯基-N′-(1-甲基-3-乙基-4-氯-5-吡唑甲酰基)脲(2a~2f)和6个新的N-取代苯基-N′-(1-甲基-3-乙基-4-氯-5-吡唑甲酰基)硫脲(3a~3f),收率44%~89%。2和3的结构经1H NMR,IR和元素分析表征。用叶片浸液法测定了2和3对红蜘蛛的毒杀作用,初步实验结果表明它们有一定的杀螨活性。     

N-(1, 3, 4-噻二唑-2-基)-N′-芳酰基脲的合成及其生物活性

2-氨基噻二唑与芳酰基异氰酸酯反应合成了13种N-(1,3,4-噻二唑-2基)-N'-的芳酰基脲,产率为54.5%～86.2%. 用核磁共振氢谱、红外光谱和元素分析确证了目标化合物的结构,室内的生物活性测定试验表明,目标化合物中的2b、2c、2e和2h具有优良的植物生长调节活性.     

N-1，3，4-噁二唑基-N′-呋喃甲酰基硫脲的合成及杀菌活性研究

N-1;3;4-噁二唑基-N′-呋喃甲酰基硫脲的合成及杀菌活性研究;呋喃;噁二唑;酰基硫脲;合成;杀菌活性     

N-1，3，4-噁二唑基-N′-呋喃甲酰基硫脲的合成及杀菌活性研究

N-1;3;4-噁二唑基-N′-呋喃甲酰基硫脲的合成及杀菌活性研究;呋喃;噁二唑;酰基硫脲;合成;杀菌活性     

酰基硫脲的合成、性质及生物活性

综述了近年来酰基硫脲类化合物的的合成,性质及生物活性的研究进展,参考文献22篇。     

The chromatography of metal chelates

Summary The acyl substituents of N,N-disubstituted N'-acylthioureas have a significant influence on the polarity of the chelates formed. A considerable decrease in the stability of the complexes is observed changing from aromatic to aliphatic acyl substituents. In order to separate the acylthiourea complexes, high performance thin-layer chromatography (HPTLC) methods have been used, whereby both standard methods, adsorption chromatography on silicagel layers and RP-chromatography are applicable. The strong UV-absorption properties of acylthiourea chelates allow a very sensitive detection of the separated complexes. By the method described several metals can be determined simultaneously on a migration distance of 2 to 5 cm.     

Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis,molecular geometry,theoretical studies and biological applications

Two mononuclear ruthenium complexes ( 1 and 2 ) with aroyl/acylthiourea as an ancillary ligand of type, [(η⁶‐p‐cymene)RuCl(L‐N,S)], where [ L1  = 2,4‐dichloro‐N‐(o‐tolylcarbamothioyl)benzamide] and L2  = N‐(phenylcarbamothioyl)cyclohexanecarboxamide] were synthesized and well characterized. The single crystal X‐ray diffraction studies revealed the coordination mode and the geometry of the complexes. The two complexes adopted general piano‐stool (three‐legged) geometry with a novel coordination mode of aroyl/acylthiourea through amide N (anionic) and thiocarbonyl S (neutral). This type of monobasic bidentate coordination of the aroyl/acylthiourea ligand was witnessed the first time around the metal ion. The coordination of the complexes was well explained through geometric parameters and frontier molecular orbital parameter values computed at the B3LYP/SDD level. The synthesized complexes were also screened for their antibacterial, antifungal, antioxidant and in vitro antiproliferative activities. Complexes exhibited good antimicrobial agents against various pathogens. The antioxidant activity of the complex 2 has shown most potent activity with IC₅₀ value of 48.55 ± 1.7 μM compared to the reference drug. In addition, the in vitro antiproliferative activity of the complex 2 showed excellent activity against HepG‐2 cell line with the IC₅₀ value of 24.30 ± 1.20 μM which is close to Doxorubicin standard drug.     

A quantum mechanical study of the stability and structural properties of substituted acylthiourea compounds

The conformational, structural and electronic properties of eight acylthiourea derivatives with the general form N-acyl-N′, N′-alkylthiourea have been investigated computationally at the MP2 level of theory and the 6-311G(d) basis set. Transition states between the four stable conformations were identified and characterized. There is a good correlation between the electron density at the bond critical point of each of the three C–N bonds present in the molecules, the calculated bond length, and the rotational barrier around these bonds. The calculations suggest the C(S)-N′ bond to have considerable double bond character which, according to analysis in terms of the Natural Bond Orbitals paradigm, can be attributed to a more favorable delocalization of the N′ lone pair into the antibonding π*(C=S) orbital than the lone pair on the other nitrogen. The influence of the various substituents on the structural and energetic features of the acylthiourea backbone is also investigated.     

Coerced photodimerization reaction in the solid state through amine salt formation

Photodimerization of fumaric or several γ-form trans-cinnamic acids proceeded successfully in the solid state through amine salt formation with ammonia or some aromatic heterocyclic amines (especially, imidazole). It appears that this success is due to a small size or a planar structure of the amine. A layered or a channel-type clathrate crystal structure was revealed, respectively.     

A high hydroarylation activity of K2PtCl4/AgOTf catalyst in the reaction of propiolic acid with unactivated and activated arenes

A mixed catalyst K₂PtCl₄/AgOTf showed the highest activity for hydroarylation of propiolic acid, among palladium and platinum catalysts. This catalyst was effective for hydroarylation with less reactive benzene to give cis-cinnamic acid in good yield. The hydroarylation with toluene gave a higher yield of hydroarylation products than that with benzene and resulted in ortho/para orientation with an almost statistical ratio, suggesting that the result is very close to that of the Friedel-Crafts alkylation with methyl bromide or p-nitrobenzyl chloride. Hydroarylation of propiolic acid with other electron-rich arenes proceeded efficiently in the presence of the K₂PtCl₄/AgOTf catalyst in trifluoroacetic acid forming cis-cinnamic acids in good to high yields. This method was also applied to hydroarylation of ethyl propiolate.