- An Expedient Method for the Synthesis of 1,2,4-Triazolo-fused 1,5-Benzodiazepine, 1,5-Benzoxazepine, and 1,5-Benzothiazepine Scaffolds: A Novel Seven-membered Ring System of Biological Interest
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New heterocyclic compounds 1-(3-methyl-9H-dibenzo[b,f][1,2,4]triazolo[4,3-d][1,4]diazepin-6-yl)ethanone 8a, 1-(3-methyldibenzo[b,f][1,2,4]triazolo[4,3-d][1,4]oxazepin-6-yl)ethanone 8b, and 1-(3-methyldibenzo[b,f][1,2,4]triazolo[4,3-d][1,4]thiazepin-6-yl)ethanone 8c are synthesized from benzodiazepinone, benzoxazepinone, and benzothiazepinone derivatives. These heterocyclic scaffolds have wide medicinal importance. Best results were obtained in antibacterial screening against Escherichia coli, Enterobacter cloacae, and Staphylococcus aureus and antifungal screening against Candida albicans and Fusarium oxysporum. 1,1-Diphenyl-2-picrylhydrazyl radical scavenging activities of compounds 6c, 7c, and 8c were tested in doses 10, 20, 30, 40, and 50?μg/mL and were expressed as IC50 values and percent of inhibition with means?±?standard deviation of three different concentrations of synthesized compounds. The assignment of the structures of synthesized compounds was made by thin-layer chromatography, elemental analysis, IR, 1H-NMR, 13C-NMR, and liquid chromatography–mass spectrometry.
- Sharma, Aruna,Kishore, Dharma,Singh, Bhawani
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- Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions
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A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.
- Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu
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p. 12344 - 12353
(2021/09/02)
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- Method for synthesizing 1-(5-benzothiazolyl)ethyl ketone
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The invention discloses a novel method for synthesizing 1-(5-benzothiazolyl)ethyl ketone. The method takes para-chloroacetophenone, concentrated sulfuric acid, concentrated nitric acid, sodium sulfidenonahydrate, zinc powder and formic acid as raw materials, and the synthesis of the 1-(5-benzothiazolyl)ethyl ketone can be realized under relatively moderate conditions. According to the novel method disclosed by the invention, the raw materials have low cost and the economic benefits are relatively high; reaction conditions are relatively moderate, the reaction speed is relatively rapid and theconversion rate is relatively high; the method is safe and environmentally friendly and is simple to operate; the method is more easily applied to synthesis of organic intermediates.
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Paragraph 0024; 0025; 0032; 0039; 0046; 0053
(2018/12/13)
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- Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships
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Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.
- Zhang, Shao-Lin,Yang, Zheng,Hu, Xiaohui,Tam, Kin Yip
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supporting information
p. 3441 - 3445
(2018/09/29)
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- Vanadium pentoxide as a catalyst for regioselective nitration of organic compounds under conventional and nonconventional conditions
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Vanadium pentoxide is used as an efficient catalyst for regioselective nitration of aromatic compounds under conventional and nonconventional conditions such as ultrasonically assisted (USAR) and microwave-assisted reactions (MWAR). The reactions underwent smoothly and afforded good yields of products with high regioselectivity. Observed longer reaction times (about 8 h) in V2O5 catalyzed reactions reduced to (0.5/30 min) under sonication and (90 s) in the case of MWAR. When ortho position is blocked, para derivatives are obtained as end products while ortho nitro products are obtained when para position is blocked.
- Venkatesham,Reddy, K. Rajendar,Rajanna,Veerasomaiah
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p. 921 - 926
(2014/04/03)
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- Synthetic studies on N-methyl piperazine containing pyrazoles and their ethoxyphthalimide derivatives
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In the present investigation, synthesis of 1-{4-[5-aryl-1-(N- ethoxyphthalimido)-4,5-dihydro-1H-pyrazol-3-yl]-2-nitrophenyl} -4-methylpiperazine (6a-d) via a series of reactions was carried out. For this purpose 4-N-methyl piperazinyl-3-nitro acetophenone (2) was prepared by the nitration of 4-chloroacetophenone, followed by addition reaction with N-methyl piperazine in isopropanol, which on condensation with various aldehydes (3a-d) gave 3-aryl-1-[4-(4-methylpiperazin-1-yl)-3-nitrophenyl]prop-2-en-1-one (4a-d). Arylidine derivatives (4a-d) were further cyclized to their corresponding pyrazole derivatives (5a-d) by reaction with hydrazine hydrochloride in DMF. Furnished the final compounds (6a-d) through subsequent treatment of 1-{4-[5- aryl -4,5-dihydro-1H-pyrazol-3-yl]-2-nitrophenyl}-4-methylpiperazine (5a-d) with N-hydroxyphthalimide in the presence of NaH in DMF. All the synthesized compounds have been characterized by elemental analysis and spectral data.
- Joshi, Ajit,Sain, Devendar,Hussain, Nasir,Talesara, G. L.
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p. 5933 - 5936,4
(2020/09/15)
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- Tricyclic compounds and drug compositions containing the same
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Compounds having a β-3 adrenaline receptor agonist and are useful as drugs for the treatment and prevention of diabetes, obesity, hyperlipemia, etc., represented by a general formula (I) and salts thereof, and a process for producing these, and their intermediates, wherein R represents hydrogen or methyl; R1 represents hydrogen, halogen, hydroxy, benzyloxy, amino, or hydroxymethyl; R2 represents hydrogen, hydroxymethyl, NHR3, SO2 NR4 R4', or nitro; R6 represents hydrogen or lower alkyl; and X represents nitrogen, R9 represents hydrogen, one of R7 and R8 represent hydrogen, and the other thereof represents hydrogen, amino, acetylamino, or hydroxy.
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- Synthesis of &β-amino substituted 4-amino-3-nitropropiophenones as diethylcarbamazine analogs and their antifilarial activity
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A number of β-amino substituted 4-amino-3-nitropropiophenones (5-16) have been synthesised and evaluated against filariasis.Compounds 14,10 and 13 show 77.5percent, 74.4percent and 82.2percent microfilaricidal activity respectively, at 30 mg/kg for 5 days by i.p. route.Compound 14 also show 60.3percent adulticidal activity.
- Varma, Rajendra S,Sarin, Simi,Chatterjee, R K
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p. 711 - 713
(2007/10/02)
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- Process for the production of nitro derivatives of aromatic compounds
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Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.
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- Substituted alkylaryl ketones and methods of use as herbicides
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Ring and side chain substituted alkylaryl ketones are useful in controlling the growth of germinating and seedling weed grasses and germinating and seedling broadleaf weeds.
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