新型1,1-二氧代-4H-苯并[1,2,4]-噻二嗪类衍生物的合成及其抗肿瘤活性

以2-硝基苯磺酰氯为起始原料,经多步反应合成了12种新型1,1-二氧代-4H-苯并[1,2,4]-噻二嗪类衍生物,产物收率高,水溶性好,并经¹H NMR、¹³C NMR、MS-ESI和元素分析法确证结构。 用MTT法测试了这类衍生物对肝癌细胞HepG-2生长的抑制作用,结果显示目标化合物能不同程度地抑制肿瘤细胞生长,其中7-氨甲基-3-环丙基-1,1-二氧代-4H-苯并[1,2,4]-噻二嗪 (7c)对肝癌细胞HepG-2的抗性显著,最高抑制率达到79.3%。     

Facile Synthesis of 4H-1,2,4-Benzothiadiazine-1,1-dioxides

A short and efficient synthesis of the title compound based on racemate resolution is described.     

Novel Synthesis of a 2H-1,2-Benzothiazine -1,1-Dioxide Derivative

We report a novel synthesis of 4-chloro-2-cyclohexyl-6,7-dimethoxy-2H-1,2-benzothiazine-1,1-dioxide 6 from 3,4-dimethoxychalcone 1. Chlorosulfonation of 1 followed by amination, then epoxidation under basic conditions with immediate elimination of the benzoyl group and electrophilic chlorination resulted in 6. A mechanism is suggested.     

Synthesis of 3-carbamoyl-1,2,4-oxadiazoles

A convenient method for the synthesis of 3-carbamoyl-1,2,4-oxadiazoles from carbamoylamidoximes and chlorides or anhydrides of haloacetic acids was developed. The reactions of 3-carbamoyl-5-trichloromethyl-1,2,4-oxadiazoles with amines and N,N-dimethylhydrazine were studied.     

5-取代-1H-1,2,4-三氮唑-3-羧酸的合成及结构表征

以5-氨基-1H-1，2，4-三氮唑-3-羧酸为原料，经重氮化反应和Sandmeyer反应得到5-X(X=Cl，Br，I，CN)-1H-1，2，4-三氮唑-3-羧酸，通过元素分析、UV，IR，1H NMR和MS对所有产物的结构进行了表征。     

微波辅助一步合成2-取代吲哚

微波辐射下以取代苯胺1, 2-溴芳基乙酮2为原料, 在无催化剂条件下一步合成了一系列2-取代吲哚3. 该方法具操作简单、反应时间短、产率高等特点.     

Synthesis,Antiviral, and Antimicrobial Activity of 1,2,4-Triazole Thioglycoside Derivatives

Abstract

The reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with glucosyl, galactosyl, lactosyl bromide, and peracetylated ribose under the conventional and microwave irradiation methods afforded the corresponding S-glycosides. Deacetylation of S-glycosides gave the corresponding deacetylated derivatives. Reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with 4-acetoxybutyl bromide, 2-acetoxyethoxymethyl bromide, 3-chloropropanol, 1,3-dichloroopropan-2-ol, epichlorohydrin, allyl bromide, and propargayl bromide gave the corresponding S-acyclonucleosides, which were deacetylated to give the corresponding deacetylated compounds. All the newly synthesized compounds were characterized by the IR, ¹H, ¹³C NMR, and elemental analyses. Some of these compounds were screened for their antiviral and antimicrobial activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the related elements to view the free supplemental file.     

Microwave-Assisted Synthesis of Some Pyrimidine Derivatives

Oxo-and thioxopyrimidines 4a–i were synthesized using the Biginelli three-component cyclocondensation reaction of an appropriate β-diketone, arylaldehyde, and (thio)urea under microwave irradiation. Yields of products following recrystallization from ethanol were of the order of 65–90%. ¹H and ¹³C NMR spectroscopy and elemental analysis were used for structural assignment.     

微波辅助合成双1,2,4-三嗪化合物及其荧光特性研究

以联苯甲酰、二甲酰肼为原料, 采用微波技术合成了5个双1,2,4-三嗪化合物3, 产率72%～85%, 利用元素分析、MS, IR, ¹H NMR和荧光光谱对其结构进行了表征, 并研究了金属离子对化合物3a的荧光性质的影响. 结果表明, 微波合成具有缩短反应时间、提高产率的优点; Cu^2＋, Ni^2＋等金属离子对化合物3a产生明显的荧光猝灭作用.     

微波促进下3-(2-苯并呋喃基)-4-氨基-5-巯基-1,2,4-三唑

微波辐射条件下, 首先由2-苯并呋喃甲酰肼依次与二硫化碳和水合肼反应合成3-(2-苯并呋喃基)-4-氨基-5-巯基- 1,2,4-三唑, 进一步在微波辐射条件下由4-氨基-5-巯基-1,2,4-三唑分别与芳甲酸/芳氧基乙酸、α-溴代苯乙酮及芳醛反应以较高产率制得了相应的1,2,4-三唑并[3,4-b]-1,3,4-噻二唑、1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪及4-芳亚甲基亚胺基-5-巯基-1,2,4-三唑. 产物结构经IR, ¹H NMR, MS及元素分析进行了表征.     

二芳基取代-1,2,4-三唑类化合物的合成及其抗炎活性研究

以选择性环氧化酶-2(COX-2)抑制剂Celecoxib为先导,根据其构效关系和分子模拟研究结果,应用生物电子等排原理等药物设计方法,设计合成了19个结构全新的二芳基取代-1,2,4-三唑类衍生物,其结构经IR,¹HNMR,MS和元素分析确证.初步的药理试验结果表明,部分目标化合物具有一定的抗炎活性.     

2-(3-芳氧甲基-4-苯基-1,2,4-三唑-5-硫基)乙酸的微波合成及生物活性研究

在微波辐射条件下, 芳氧乙酰肼经两步反应制得4-苯基-3-芳氧甲基-1,2,4-三唑-5-硫酮衍生物, 再与氯乙酸反应得到6种尚未见文献报道的2-(3-芳氧甲基-4-苯基-1,2,4-三唑-5-硫基)乙酸衍生物. 目标化合物的结构经IR, ¹H NMR和元素分析进行了确证. 生物活性试验结果表明, 该类化合物对双子叶植物油菜具有良好的生物调节活性.     

Synthesis of Biological Active Chromene Benzothiadiazole Derivatives

In this article, we describe the synthesis of various substituted Chromene-[1, 3]thiazolo [2, 1, 3] benzothiadiazoles 4a-l by conventional (Method A) and microwave-assisted (Method B) which achieved reductions in reaction times, higher yields, and a cleaner reaction than the conventional method. A comparative study of these two methods has been discussed.     

微波促进下4-芳基亚氨基-1,2,4-三唑的合成

无溶剂;无催化剂;微波辐射;取代基-巯基-芳基亚氨基三唑     

Synthesis of 1,3,5-Trisubstituted 1H-1,2,4-Triazoles Containing Hetaryl Fragments

N¹-Phenyl- and N¹-(3,5-dichloro-2-pyridyl)amidrazones have been synthesized by the reaction of imino esters of heterocyclic acids with phenyl- or (3,5-dichloro-2-pyridyl)hydrazine. Acylation of the products with acid chlorides leads to 1-phenyl- and 1-(3,5-dichloro-2-pyridyl)-3-hetaryl-5-R²-1H-1,2,4-triazoles. Compounds of this type are also formed by the condensation of N-acylimino esters of heterocyclic acids with phenyl- or (3,5-dichloro-2-pyridyl)hydrazine.     

1,1-二苄基-1,1-二硫乙酰腙甲烷类化合物的微波辐射法合成

以1,3-二苯基丙酮为原料,经干燥的H2S和HCl气体反应得二苄基二巯基甲烷(1),在微波辐射条件下,经酯化、肼解,得l,1-二苄基-1,1-二硫乙酰肼(3),再与芳香醛反应,方便地合成了酰腙类新化合物(4a～4n).其结构经IR、1H NMR、MS和元素分析确证.     

Microwave-Assisted Solid-Phase Synthesis of Cephalosporin Derivatives with Antibacterial Activity

Summary.  The reaction of heterocyclic acids with 7-amino-cephalosporanic acid adsorbed on basic alumina under microwave irradiation afforded the N-acylated cephalosporin analogues in satisfactory yield. All compounds were tested for their antibacterial activity; some of them showed significant antibacterial properties. Cefotaxime and cephalothin were used as reference drugs. Received February 23, 2000. Accepted March 28, 2000     

Green,Microwave-Assisted Approach to the Synthesis of Arylidene-Substituted Spiro[4,5]decan-8-one Derivatives in Water

A green approach to the synthesis of arylidene-substituted spiro[4,5]decan-8-one derivatives was successfully realized via the mild, base-catalyzed reaction of aromatic aldehydes with 1,4-dioxa-spiro[4.5]decan-8-one in water under microwave irradiation. This protocol has the prominent advantages of environmental friendliness, short reaction time, excellent yields, low cost, easy operation, and broad scope of applicability.     

Studies on 1, 2, 4-Benzothiadiazine 1, 1-Dioxide IX.1 Synthesis and Pharmacological Evaluation of 1, 2, 4-Benzothiadiazine 1, 1-Dioxide Biphenyl Tetrazoles as Angiotensin II Antagonists

In the course of our investigations on the development of cardiovascular agents, 3-butyl-2-[2′-(2H-tetrazol-5-yl)bipheny]-4-yl]methyl-2H-1, 2, 4-benzothiadiazine 1, 1-dioxide ( 2 ) was considered as a potential angiotensin II antagonist on the basis of bioisosteric replacement of the quinazoline ring of compound 1 with a 1, 2, 4-benzothiadiazine 1, 1-dioxide ring system. Alkylation of 6 with 4 afforded 7 and 8 in 24% and 28% yields, respectively. An attempt to remove the trityl group of compounds 7 and 8 under acidic condition gave the ring opened products 9 and 11 in 28% and 36% yields, respectively. However, compounds 2 and 10 were obtained in 46% and 85% yields when compounds 7 and 8 were refluxed in methanol. Preliminary assays of compounds 9 and 11 against angiotensin II receptors revealed weak activity with IC₅₀ values of 3.6 μM and 5.4 μM, respectively. Compound 10 (IC₅₀ = 87 nM) exhibited stronger binding affinity than compound 2 (IC₅₀ = 750 nM).