N′叔丁氨基羰基-N-(5-取代苯基-2-呋喃甲酰基)硫脲的合成及对白血病K562细胞增殖的影响

合成;N′-叔丁氨基羰基-N-（取代苯基呋喃甲酰基）硫脲;MTT法;白血病K562细胞     

N′-叔丁胺基羰基-N-取代菊酰硫脲类化合物的合成及生物活性测定

拟除虫菊酯类和酰基硫脲类化合物具有很好的杀虫 ,杀菌及植物生长调节活性[1 - 3] 。本文采用有效基团拼接方法 ,以拟除虫菊酯类化合物的活性部分即取代菊酸为母体 ,以酰基硫脲为骨架 ,并将叔丁基引入到该结构中 ,设计合成了 4种N 叔丁胺基羰基 N 取代菊酰硫脲类化合物。结构经1 HNMR ,IR和元素分析表征 ,初步的生物活性测定结果表明该类化合物具有较好的生物活性合成路线为 ,其结构简式如下发 :1　实验部分1 1　仪器和试剂XT4A型显微熔点测定仪 ;Nicolet5DXFT IR型红外光谱仪 (KBr压片 ) ;joelFX 90Q型超导核磁仪 (CDCl3作溶…     

N-取代芳酰氨基-5-氟代苯基-2-呋喃甲酰硫脲的合成与生物活性测定

从5-氟代苯基-2-呋喃甲酸出发, 经酰化、异硫氰酸酯化, 再与取代芳酰肼反应合成了20个未见文献报道的N-取代芳酰氨基-5-氟代苯基-2-呋喃甲酰硫脲. 目标产物的结构经IR, ¹H NMR和元素分析测定确证. 初步生物活性测试表明, 部分化合物对棉花枯萎病、黄瓜灰霉病、苹果轮纹病和棉花炭疽病有较好的选择性杀菌活性; 部分目标化合物有较好的除草活性.     

(R)-α-苯乙胺拆分全顺式-3-N-叔丁氧羰基氨基-5-甲氧羰基环己基甲酸

以光学活性(R)-α-苯乙胺(1)为拆分剂,将cis,cis-3-N-叔丁氧羰基氨基-5-甲氧羰基环己基甲酸[(±)-2]拆分为cis,cis-(-)-2,其结构经1H NMR和13C NMR确证。最佳拆分条件为:以丙酮为溶剂,n(1)∶n[(±)-2]=1.0∶1.0,拆分效率34.1%。     

N′-叔丁基-N-取代酰基(硫)脲类化合物的合成及生物活性测定

将叔丁基引入到酰基 (硫 )脲骨架中 ,设计合成了 8个未见文献报道的N′ 叔丁基 N 取代酰基脲及N′ 叔丁氨基羰基 N 取代酰基硫脲类化合物 ,其结构经元素分析、IR和1 HNMR得到确证 .初步的生物活性测试结果表明部分化合物具有较好的除草活性     

N-(取代苯氧乙酰基)-N'-(4-苯基噻唑-2-基)硫脲的合成

以取代苯酚和氯乙酸为原料,合成取代苯氧乙酸,然后经过酰氯化,酯化得到取代苯氧乙酰基异硫氰酸酯,再和2-氨基-4-苯基噻唑反应得到4种N-(取代苯氧乙酰基)-N'-(4-苯基噻唑-2-基)硫脲类化合物,其中3种化合物为首次报道。化合物结构经1H NMR、IR和元素分析得到确证。初步室内生测结果表明该类化合物具有一定的抑菌活性。     

N-[5-(2-氯苯基)-2-呋喃甲酰氨基硫羰基]-L-α-氨基酸乙酯的合成与生物活性测定

设计并合成了9种未见文献报道的N-(5-邻氯苯基-2-呋喃甲酰氨基硫羰基)-L-α-氨基酸乙酯衍生物,其结构经IR,1H NMR,MS和元素分析测试确证.MTT法测试结果表明大部分目标化合物对白血病K562细胞系的增殖具有明显的抑制作用.     

N-芳基-N''''-(5-芳基-2-呋喃甲酰基)硫脲衍生物的合成及其生物活性的研究

于固-液相转移条件下,合成了40个未见报道的N-芳基-N'-(5-芳基-2-呋喃甲酰基)硫脲衍生物,用元素分析、UV、IR以及~1H NMR光谱确定了它们的结构.该法具有操作简便、反应条件温和、产率高等优点.初步生物活性试验表明,该类化合物对小麦幼苗生长有明显的促进作用.     

S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙酸硫酯类化合物脱除Boc保护基的反应研究

报道了取代苯丙酸类化合物1a～1d与N-叔丁氧羰基-L-半胱氨酸甲酯(2)在双(2-氧代-3-噁唑烷基)次磷酰氯(BOP-C1)作用下,以79%～92%收率得到缩合产物S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙酸硫酯类化合物3a～3d;3a～3d在三氟乙酸(TFA)作用下脱除Boc保护基时,结果不仅得到了正常的脱保护基产物4a～4d,还生成了2-取代噻唑啉类化合物5a～5d,研究表明5a～5d是由4a～4d分子内脱水环合而成.通过优化三氟乙酸用量、反应温度以及反应时间等条件,能够以较高收率分别得到4a～4d和5a～5d(收率85%～91%和86%～89%).而S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙烯酸硫酯类化合物3e～3f由于双键结构,在三氟乙酸作用下仅生成脱除Boc保护基产物4e～4f.该反应的研究为2-取代噻唑啉类化合物的合成提供了一种简便有效的方法.     

N'-(5-芳基-1,3,4(口恶)二唑-2-基)-N-(邻苯磺酰甲酰亚胺乙酰基)硫脲的合成及抑菌活性

将邻苯甲酰磺酰亚胺、1.3,4-(口恶)二唑2个杂环同时引入到酰基硫脲中,合成了12种新的N'-(5-芳基-1,3,4.(口恶)二唑-2-基)-N-(邻苯磺酰甲酰亚胺乙酰基)硫脲化合物,化合物的结构均经元素分析、1H NMR和IR 等测试技术得以确证.抑菌法生物活性测试结果表明,大部分化合物对黄瓜灰霉病菌、油菜菌核病菌抑制效果很好,特别是化合物5b和5l对5种病菌抑制率均在87%以上,有的病菌抑制率达到100%.     

Synthesis, Crystal Structure and Inhibition of the K562 Cell Proliferation of N＇-Tertbutylaminocarbonyl-N-2-chlorophenoxyacetylthiourea

The title compound N'-tert-butylaminocarbonyl-N-2-chlorophenoxyacetylthiou- rea has been synthesized for the first time. Complete assignments were achieved by IR, 1H NHR and single-crystal X-ray diffraction analyses. The inhibitory rate of the cellular growth of K562 cells (chronic myeloid 1eukemic cells) was measured using MTT [3-(4,5-dimethylthiazo-2-y1)-2,5-di- phenyltetra-zolium bromide] assay. The cell apoptosis was assessed by agarose gel electrophoresis to find that the title compound has antiproliferation and apoptosis inducing effects on K562 cells. In order to investigate the relationship between structure and activity of the target compound, we report its crystal structure and biological behavior in the present paper. Crystallographic data: C14H18- ClN3O3S, Mr = 343.82, orthorhombic, space group Pnma, a = 19.786(6), b = 6.789(2), c = 12.938(4) , V = 1738.0(9) 3, Z = 4, Dc = 1.314 g/cm3, F(000) = 720, μ(MoKα) = 0.354 mm-1, R = 0.0378 and wR = 0.0941. The molecule is a planar structure.     

Synthesis, Crystal Structure and Inhibition of N-2-Thiophenesulfonyl-a-L-phenylalanine Ethyl Ester on K562 Cell Proliferation

The title compound N-2-thiophenesulfonyl-a-L-phenylalanine ethyl ester has been synthesized. Complete assignments were achieved by IR, MS, ^1H NMR and single-crystal X-ray diffraction analyses. Using MTT assay, the inhibitory rate of the title compound on K562 cells （chronic myeloid leukemic cells） was measured and the result of preliminary bioassay showed that the title compound possesses antiproliferation effects on K562 cells. In order to investigate the relationship between structure and activity of the target compound, we report its crystal structure and biological behavior in the present paper. Crystallographic data： C15H17NO4S2, Mr = 339.42, monoclinic, space group P21, flack = -0.15（12）, a = 5.7916（10）, b = 11.5078（19）, c = 12.924（2） A, β = 97.781（3）°, Z = 2, V = 853.4（2） A^3, De = 1.321 g/cm^3, F（000） = 356, -7≤h≤7, -10≤k≤14, -15 ≤ l≤15, R = 0.0628, wR = 0.1540 and μ（MoKa） = 0.327 mm^-1. The molecule comprises a benzene and a thiofuran rings, and the intramolecular N（1）-H（1A）…O（1） makes a five-membered ring of O（1）--C（6）-C（5）--N（1）--H（1A）.     

硒化壳聚糖抗K562细胞的实验研究

用MTT法和AO/EB荧光染色法观察了硒化壳聚糖对K 562肿瘤细胞株生长的影响。结果发现,硒化壳聚糖可有效地抑制K 562细胞生长,并呈量效、时效关系。经硒化壳聚糖作用后的细胞可明显出现核固缩、碎裂等凋亡形态改变。硒化壳聚糖可诱导K 562细胞凋亡,抑制其生长。     

一些吲哚二酮类衍生物的合成及对AHAS的抑制活性

基于一些新结构特征的AHAS抑制剂, 设计并合成了一系列吲哚二酮类化合物. 初步的生物活性测试结果表明, 所合成的化合物在体内和体外均具有一定的生物活性, 其中, 化合物13在100 μg/mL浓度下对AHAS的抑制达到85%, 化合物7(平皿法)在100 μg/mL浓度条件下对油菜胚根生长抑制率可达84.7%, 是一类未见文献报道的结构新型的AHAS抑制剂, 有望为进一步设计合成更高活性的化合物提供参考.     

Synthesis of Aminoalkyl-substituted Polymethoxychalcone Derivatives and Their Antiproliferative Activities Against Three Human Cancer Cell Lines

Two novel series of sixteen aminoalkyl-substituted polymethoxychalcone derivatives 2a-2h and 3a-3h were synthesized from 2'-hydroxy-3,4,5,4',6'-pentamethoxy chalcone(1) through extending alkoxy side chain at the 2'-position, and introducing amine hydrogen bond receptor at the end of the side chain. The structures of all the synthesized compounds were confirmed by ¹H NMR, ¹³C NMR and MS techniques. Furthermore, all the compounds were tested for antiproliferative activities in vitro against a panel of three human cell lines(HeLa, HCC1954 and SK-OV-3) via CCK-8 assay. The results show that all the target compounds exhibit antiproliferative activities against the three human cancer cells with IC₅₀ values of 4.62-48.21 μmol/L, except compound 2h against SK-OV-3 cells. Most of these compounds were more active when compared to the positive control cis-Platin.     

Aqueous Extract of Crataegus azarolus Protects Against DNA Damage in Human Lymphoblast Cell K562 and Enhances Antioxidant Activity

The present study was carried out to characterize the cellular antioxidant effect of the aqueous extract of Crataegus azarolus and its antigenotoxic potential using human myelogenous cells, K562. The antioxidant capacity of this extract was evaluated by determining its cellular antioxidant activity (CAA) in K562 cells. Also, preceding antigenotoxicity assessment, its eventual genotoxicity property was investigated by evaluating its capacity to induce the DNA degradation of treated cell nuclei. As no genotoxicity was detected at different exposure times, its ability to protect cell DNA against H₂O₂ oxidative effect was investigated, using the “comet assay.” It appears that 800 μg/mL of extract inhibited the genotoxicity induced by H₂O₂ with a rate of 41.30 %, after 4 h of incubation. In addition, this extract revealed a significant cellular antioxidant capacity against the reactive oxygen species in K562 cells.     

Design,Synthesis and Activities of Aziridine Derivatives of N5-Methyltetrahydrofolate Against Methionine Synthase

Aziridine derivatives of N⁵-methyltetrahydrofolate were designed and synthesized based on the mechanism of methionine synthase, and their biological activities were investigated as well. The aziridine derivatives 1 and 6 exhibited superior inhibitory activities(IC₅₀: 5.05 and 4.15 μmol/L, respectively) compared to the corresponding chain analogue 4(IC₅₀=24.42 μmol/L). The results suggest that the aziridine derivatives can get potential activities against nucleophilic methionine synthase.     

单独和合用硒化壳聚糖与阿霉素对K562细胞作用的研究

应用MTT法和AO／EB荧光染色法观察单独和合用硒化壳聚糖与阿霉素对K562细胞株的影响,结果发现硒化壳聚糖和阿霉素均可有效地抑制K562细胞生长。且两药联合使用效果更佳。硒化壳聚糖可诱导细胞凋亡。两药合用诱导细胞凋亡效果更好。     

微波辐射下5-取代-2-硫代海因衍生物的合成

微波辐射下, 由硫氰酸铵与α-氨基酸通过两步反应合成了11种5-取代-2-硫代海因衍生物, 并用¹H NMR, IR和元素分析确证了中间产物和终产物的结构. 对比常规加热方法, 微波辐射具有反应时间短(4 min), 每步反应产率高(85%～93%)的优点. 同时对合成化合物2h的反应历程进行了讨论.