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CONDENSATION OF o-AMINOTHIOPHENOL WITH ALDEHYDES
Although the sulfur atom is relatively unreactive, the flankingcarbon centers, the 2- and 5-positions, are highly susceptible toattack by . Halogens give initially2-halo derivatives followed by 2,5-dihalothiophenes;perhalogenation is easily accomplished to giveC4X4S (X = Cl, Br, I).Thiophene brominates 107 times faster than doesbenzene.
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Objective: Synthesis of novel pyrazolines (P2-P4 & P7-P9) from the chalcones (C2-C10) obtained by condensing different aldehydes with 2-acetyl- 5-bromothiophene and evaluates them for in vitro anticancer and anti-inflammatory activities.
COUPLING BETWEEN THIOPHENOLS AND AROMATIC NITRILES
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Due to these biological activities, the synthesis of benzothiazole is a considerable area of current discussion. The classical method involves condensation of o-aminothiophenols with substituted aldehydes 8-14, acyl chlorides, carboxylic acids 15-16 or esters, nitriles 17. Other most commonly used methods include Pd/Cu/Mn/chloranil catalyzed cyclization of o-halothioformanilides 18-22. The survey of literature related to benzothiazoles reveals the presence of this bicyclic ring system in various amine or terrestrial natural compounds, which have useful biological properties 23. Benzothiazole derivatives possess a wide spectrum of biological applications such as antitumor 26-52, antimicrobial 54-83, schictosomicidal 84, anti-inflammatory 85-93, anticonvulsants 94-102, antidiabetic 103-108, antipsychotic 109 and diuretic 111 etc.
Polycyclic aromatic hydrocarbons (PAHs) represent an important class of fundamental pai-systems. Triphenylene, one of the simplest framework of PAHs, and its derivatives have been extensively investigated in terms of their unique structures and properties. To further modulate their inherent structural and electronic features, many benzo derivatives have been synthesized. On the other hand, the incorporation of thiophene rings onto PAHs exhibits considerable success in the design of unique organic semiconductors. In this context, we have previously reported the synthesis, properties, and bowl-shaped structure of hexathienotriphenylene that is formally isoelectronic with coronene. Here, we report on the synthesis, structure, and properties of novel six-thiophene-annelated triphenylene 1, which is isoelectronic with hexabenzotriphenylene .
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At room temperature, thiophene is a colorless liquid with amildly pleasant odor reminiscent of , with which thiophene shares somesimilarities. The high reactivity of thiophene toward sulfonationis the basis for the separation of thiophene from benzene, whichare difficult to separate by due to their similar boilingpoints (4 °C difference at ambient pressure). Like benzene,thiophene forms an with water.
Thiophene is produced on a scale of ca. 2M kg per yearworldwide. Production involves the vapor phase reaction of a sulfursource, typically , and . These reagents arecontacted with an oxide catalyst at 500-550 °C.
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0.01 Mol (2.05g) of 2-acetyl-5-bromothiophene taken in a 100 ml round bottom flask containing 20 ml of ethanol, to that equimolar quantity of substituted benzaldehydes added. The contents of the flask were stirred continuously using a magnetic stirrer, and the temperature was maintained below 20 ° C. Then 0.1 ml of 40% KOH was added drop by drop to the flask. The reaction was monitored by using a precoated TLC plate. After completion of the reaction, the contents of the flask were neutralized with dilute HCl to get precipitates of chalcones & filtered, washed with cold ethanol, dried and recrystallized from ethanol.
As a part of our research work, we synthesized a series of 1-(5-bromothiophen-2-yl)-3-(phenyl) prop-2-en-1-one and 1-(3-(5-bromo-thiophene-2-yl)-5-(aryl)-4,5-dihydropyrazole-1-yl) ethanone and tested biologically. The method followed for the synthesis of the final compounds is in accordance with the literature . Later, the anticancer activity of compounds was reported by screening against human breast cancer cell lines MCF-7 and MDA-MB-468 and in vitro anti-inflammatory activity was done by inhibition of bovine albumin denaturation method and heat induced hemolytic method.
Compound C 9: (2E)-1-(5-bromothiophen-2-yl)-3-phenylprop-2-en-1-one
For centuries, cancer has been prevailing as most serious disease and its incidence is rising day-to-day in the world. Cancer treatment usually falls into the category of surgery, radiation and chemotherapy. Despite of all these treatments, cancer is still continuing as uncontrollable disease and exploring for new approaches in anticancer therapy. Chemotherapy is generally used to treat cancer that has spread or metastasized because the medicines travel throughout the entire body. Recently, several substituted thiophenes and pyrazoles have been reported for anticancer activity. [1-4]. Pyrazoles substituted with another heterocyclic compound such as thiophene resulted in compounds with improved anti-proliferative activity against a number of solid and hematological tumors.  Even some prescribed drugs like omeprazole (proton pump inhibitor), eprosartan (angiotensin II receptor antagonist) and lore diplons (anxiolytic agent) have pyrazole ring connected with another heterocyclic moiety. Thiophene nucleus is also an important heterocyclic ring which is part of some of the drugs like raloxifene (osteoporosis), olanzapine (antipsychotic), and clopidogrel (antiplatelet agent). Thus, we were interested in synthesizing thiophene substituted pyrazolines and look for their anti-proliferative activity.
Thiophene is a heterocyclic compound with the formula C 4 H 4 S
Background and aim: Spiroazetidin-2-ones and furans are commonly used as anti-bacterial, anti-fungal, anti-inflammatory, cardiovascular activities, anticancer, antiparkinson agents etc. The purpose of this study was to perform virtual toxicity studies of the synthesized compounds 1-(substitutedphenyl)-3-chloro-5,9-bis(furan-2-ylmethylidene)-1-azaspiro[3.5]nonan-2-ones (3a-3h). Materials and method...
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