- One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies
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Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.
- Karthik, B.,Kumar, A. Kannan,Nukala, Satheesh Kumar,Ravinder, M.,Swamy, T. Narasimha
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p. 1269 - 1275
(2021/12/23)
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- One-pot Synthesis of Some Novel Xanthine Derived Isoxazoles as Potent Antibacterial Agents
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In search of better antibacterial agents, a series of novel xanthine derived 3,5-disubstituted isoxazole derivatives were synthesized (3a-3j) in one-pot using 8-chloro-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and aromatic aldehydes and f
- Vidya
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p. 551 - 557
(2021/02/02)
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- One Pot Synthesis and Antitumor Activity of Isoxazole-Pyrimido[4,5-c]isoquinolines
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Abstract: A number of new isoxazole coupled pyrimido[4,5-c]isoquinolines has been synthesized in good to excellent yields by the one pot method. The Cu(I)-catalyzed cycloaddition reaction between the terminal alkyne 4 and various aldehydes has led to nitr
- Venkatesh,Narsimha,Kumar,Reddy
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p. 2444 - 2450
(2021/02/16)
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- Cu(I)-Catalysis of One-Pot Synthesis of Some Novel Regioselective Isoxazole-Benzimidazole Hybrids and Their In Vitro Anti-Cancer Evaluation
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Regioselective synthesis of some novel isoxazole-benzimidazole hybrids in high yields via Cu(I)-catalyzed tandem one-pot reaction of aromatic aldehydes with 1-prop-2-ynylbenzimidazole is developed. Structures of the synthesized compounds are confirmed by
- Ashok Kumar,Shanmukha Kumar Jagarlapudib
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p. 2512 - 2515
(2020/02/25)
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- Synthesis, antimalarial activity, and target binding of dibenzazepine-tethered isoxazolines
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Malaria, a complex and deadly parasitic infectious disease, is a huge public health problem in many endemic countries around the globe. The prevailing extensive resistance of malaria parasites to traditional drugs and emergence of resistance to the currently used frontline artemisinin-based chemotherapy calls for the development of new drugs. Towards this objective and since compounds containing the dibenzazepine moiety are effective in treating both gametocyte and asexual stage malaria parasites, including multi drug resistant parasites, a library of dibenzazepine tethered 3,5-disubstituted isoxazolines was synthesised via 1,3-dipolar cycloaddition reaction. An additional diversified group of dibenzazepine derivatives were accessed by Suzuki coupling of one of the above dibenzazepine derivatives with various organoboronic acids. All compounds were structurally characterized and were evaluated for their antimalarial activity. They exhibited good to excellent inhibitory activity against the growth of drug-sensitive Plasmodium falciparum 3D7 strain with IC50 values ranging from 0.2 to 7.7 μM. About 50% of the compounds were either minimally or not toxic to human cell lines. Five of the compounds (6j, 6k, 8c, 8k and 8l) that highly inhibited the parasite growth were further assessed for antimalarial activity using an additional chloroquine-sensitive (D6) and two chloroquine-resistant (W2 and 7G8) P. falciparum strains. These compounds were effective against all four strains (3D7, D6, W2 and 7G8), exhibiting IC50 values of 0.1 to 1.75 μM. The dibenzazepines were identified to target the metalloamino-peptidase of parasites. Molecular docking and dynamics simulation studies were performed to understand the binding mode and binding strengths of the selected compounds with the enzyme. In agreement with their excellent antimalarial activity, the data suggested that the compounds can strongly bind to the active site of the enzyme.
- Vinay Kumar, Koravangala S.,Lingaraju, Gejjalagere S.,Bommegowda, Yadaganahalli K.,Vinayaka, Ajjampura C.,Bhat, Pritesh,Pradeepa Kumara, Challanayakanahally S.,Rangappa, Kanchugarakoppal S.,Gowda, D. Channe,Sadashiva, Maralinganadoddi P.
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p. 90408 - 90421
(2015/11/16)
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- Reaction of polyfluorinated cyclohexa-2,4-dienones with aryl nitrile oxides
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Reaction of 1,3-dipolar cycloaddition of 6-chloropentafluorocyclohexa-2,4- dienone, 6-chloro-3-(pentafluorophenoxy)tetrafluorocyclohexa-2,4-dienone, and perfluoro-6-phenoxycyclohexa-2,4-dienone with aryl nitrile oxides proceeds highly stereoselectively at
- Kovtonyuk,Gatilov, Yu. V.
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p. 1215 - 1220
(2013/10/01)
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- Synthesis of fluorine-containing 1,4-dioxa-2-azaspiro-[4.5]deca-2,6,9- trienes by reaction of polyfluorinated cyclohexa-2,5-dienones with nitrile oxides
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4-Pentafluorophenoxy-, 4-nitro-, and 4-chloropentafluorocyclohexa-2,5-dien- 1-ones and 3,4,5-tris-(pentafluorophenoxy)trifluorocyclohexa-2,5-dien-1-one react with some benzonitrile and acetonitrile oxides exclusively at the carbonyl group, leading to the formation of mixtures of diastereoisomeric fluorinated 1,4-dioxa-2-azaspiro[4.5]deca-2,6,9-trienes in good yield.
- Kovtonyuk, V. N.,Kobrina, L. S.,Gatilov, Yu. V.
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p. 783 - 787,5
(2020/08/31)
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- Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry
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Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.
- Yermolina, Maria V.,Wang, Jizhen,Caffrey, Michael,Rong, Lijun L.,Wardrop, Duncan J.
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p. 765 - 781
(2011/04/15)
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- REACTION OF BENZONITRILE OXIDES WITH S,S-DIMETHYL-N-(2,4,6-TRIHALOPHENYL)SULFIMIDES. THE FORMATION OF BENZOXAZOLE DERIVATIVES.
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The reactions of nitrile oxides with S,S-dimethyl-N-(2,4,6-trihalophenyl)sulfimides gave unusual products, whose structure was determined to be 2-aryl-4,6-dihalobenzoxasozles from elemental analysis and spectral data. The reactions with S,S-dimethyl-N-(2-
- Shiraishi,Hayakawa,Shigemoto
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p. 1514 - 1518
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF AZOLS AND THEIR DERIVATIVES. PART V. REGIOCHEMISTRY IN CYCLOADDITION REACTIONS OF BENZONITRILE N-OXIDE WITH β-SUBSTITUTED NITROETHYLENES
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The cycloaddition reactions of benzonitrile N-oxide with β-substituted nitroethylenes have been investigated.It was found that the regiochemistry of these reactions depended on the nature of β-substituents.
- Baranski, Andrzej
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p. 257 - 266
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF AZOLS AND THEIR DERIVATIVES. PART VI. CYCLOADDITION REACTIONS OF NITROETHYLENE WITH AROMATIC NITRILE N-OXIDES AND SOME CONVERSIONS OF 3-ARYL-5-NITRO-4,5-DIHYDRO-1,2-OXAZOLES
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Reactions of aromatic nitrile N-oxides with nitroethylene lead to formation of 3-aryl-5-nitro-4,5-dihydro-1,2-oxazoles.During heating the above compounds decompose with elimination of nitrous acid, thus affording 3-aryl-1,2-oxazoles.Under nucleophilic reagents a ring opening was observed.
- Baranski, Andrzej,Shvekhgeimer, Genrikh A.
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p. 459 - 467
(2007/10/02)
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