Synthesis and Antihypertensive Activity of 2-Imino-2,3-dihydro-5H-1,3,4-thiadiazolo[2,3-b]quinazolin-5-ones

Hydrolysis of isatoic anhydride (1) with hydrazine derivatives gave the o-aminobenzohydrazides 2a-c. Treatment of these compounds with carbon disulfide provided the 3-substituted amino-2-mercapto-quinazolin-4(3H)-ones 3a-c. Compounds 3a-c underwent cyclo-condensation with cyanogen bromide to produce th title compounds 5a-c in 56-87% yields. Preliminary pharmacological evaluation of these compounds for antihypertensive activity on anesthetized rats was accomplished.     

Chromono[2,3-b]pyrroline-2-ones (author's transl)

Chromono[2,3-b]pyrroline-2-ones The succinimide derivatives 1a , c and d condense with methyl 2-methoxybenzoate to yield the methoxybenzoylsuccinimides 2b , c and d , which are converted into the chromono[2,3-b]pyrroline-2-ones 4a , c and d with pyridine hydrochlorid or HBr/acetic acid. Reactions of these compounds are described.     

5-羟基-5H-[1]-苯并吡喃[2,3-b]吡啶的制备

目的改进5-羟基-5H-[1]-苯并吡喃[2,3-b]吡啶的合成工艺。方法以2-氯烟酸为起始原料,经亲核取代、环合和还原制得目标化合物。结果总收率68.6%,产物经熔点和1HNMR确证。结论改进后的工艺具有操作简便,对环境友好,收率高等优点。     

Hydrierte Pyrrolo[2,3-b] pyridine

Hydrogenated Pyrrolo[2,3-b]pyridines The mercuric-EDTA dehydrogenation of 1-methyl-3-(2-aminoalkyl)-piperidines gives in addition to a little 6-piperidone, mixtures of 7-methyl-2,3,3a,4,5,6-hexahydro-7H-pyrrolo[2,3-b]pyridines and 7-methyl-perhydro-pyrrolo[2,3-b]pyridines.     

2,3-Dihydro-9H-isoxazolo[3,2-b]quinazolin-9-ones and 3,4-dihydro-(1,2)-oxazino [3,2-b]quinazolin-10(2H)-ones.

Two series of compounds, 2,3-dihydro-9H-isoxazolo[3,2-b]quinazolin-9-ones and 3,4-dihydro-(1,2)-oxazino-[3,2-b]quinazolin-10(2H)-ones, were synthesized and evaluated for anti-inflammatory, antipyretic and analgesic activity. The isoxazolo compounds were generally more active than their oxazino homologs. Three compounds, i.e., 2,3-dihydro-9H-isoxazolo [3,2-b]quinazolin-9-one (W-2429) and its 2- and 3-methyl congeners, were the most active of all compounds tested in this study. On the basis of the biological results herein reported, W-2429 is considerably more effective than acetylsalicylic acid in inhibiting carrageenan-induced edema and in reducing brewer's yeast-induced fever in rats. Also, it was found to be more potent than propoxyphene hydrochloride in the Randall-Selitto test for analgesic activity.     

Synthesis and cytotoxicity of novel 6H-indolo[2,3-b]quinoxaline derivatives

A series of new 6-[(N ₁-aryl-1H-1,2,3-triazol-4-yl)methyl]-6H-indolo[2,3-b]quinoxa-line derivatives 7a _i–ix and 7b _i–vi is synthesized by a simple multi-step protocol starting from isatin 1a or 5-fluoroisatin 1b. These compounds are screened against lung (A-549), cervical (HeLa), and prostate (DU-145) human cancer cell lines to evaluate their cytotoxic effect. Of all the compounds tested, five compounds showed moderate cytotoxicity against human reproductive organ cell lines, while others exhibited lower cytotoxicity against different human cancer cell lines. An elegant synthesis of these complex molecules and their cytotoxicity data are presented.     

Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents

A series of analogues based on the 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one ring system have been synthesized and shown to possess oral antiinflammatory activity in both the reverse passive Arthus reaction (RPAR) pleural cavity assay in rats and in the adjuvant-induced arthritic rat model (AAR). Several members of this series additionally exhibit an inhibitory effect on the in vivo production of prostaglandin- and leukotriene-derived products or arachidonic acid metabolism although these compounds exhibit no significant inhibitory activity against the cyclooxygenase and 5-lipoxygenase enzymes in vitro. Structure-activity relationships in this series are discussed.     

3-Acyl-pyrano [2,3-b]indol-4-one

3-Acylpyrano[2,3-b]indol-4-ones The mixture which is obtained by treating 1-methyloxindole ( 1 ) with phosgene reacts with the alkali salts of the 1,3-dicarbonyl compounds 10a - 10d to yield the 3-acylpyrano[2,3-b]indol-4-ones 11a - 11d . Reactions with the salts of 1, 3-dimethylbarbituric acid and of 1 lead to the pyrone derivatives 12 and 13 , respectively.     

Synthesis of new 6H-indolo[2,3-b] [1,8]naphthyridines and their specific inhibition of benzodiazepine receptor

Some 3-amino- and 3-hydroxy-8-halosubstituted 6H-indolo[2,3-b] [1,8]naphthyridines were synthesized and tested for their affinity for the benzodiazepine receptor in bovine cortical membranes. All prepared compounds were more active than the corresponding 8-unsubstituted derivatives. Moreover, among these compounds the 8-chloroindolonaphthyridines were clearly the most potent.     

3-氨基-6-甲氧基噻吩并[2,3-b]喹啉-2-羧酸甲酯的合成工艺研究

目的优化3-氨基-6-甲氧基噻吩并[2,3-b]喹啉-2-羧酸甲酯的合成工艺。方法以对甲氧基乙酰苯胺为原料,经过构建喹啉环、氰基化、硫化、构建噻吩环4步反应制备目标化合物,并优化各步反应条件。结果与结论目标化合物的结构经1H-NMR、13C-NMR和ESI-MS谱确证,总收率为67.3%(以对甲氧基乙酰苯胺计),优化后的工艺路线具有收率高、操作简单、污染低、适合大量制备等优点。     

Synthesis and cytotoxicity studies of novel 2-Hydrazonylpyrido[2,3-b]pyrazin-3(4H)-ones

In an attempt to develop potent antitumor agents, a series of novel 2‐hydrazonylpyrido[2,3‐b]pyrazin‐3(4H)‐one derivatives were designed and synthesized. All the prepared compounds were screened for their cytotoxic activities against A549, MDA‐MB‐231 and HT‐29 cell lines in vitro. Pharmacological data indicated that five of the target compounds showed cytotoxicity against A549 cell line below a concentration of 1 µM. Compound 15g was the most potent one with IC₅₀ values of 0.19, 2.11 and 2.15 µM against A549, MDA‐MB‐231 and HT29 cell lines, respectively.