18439-96-8Relevant academic research and scientific papers
Development of New Molecular Entities as Potent Antifungal Agents: Synthesis of Substituted 1,2,3-Triazoles
Jeshma, K.,Kumar, A. Kishore,Ramesh, G.,Sunitha, V.
, p. 2546 - 2553 (2022/01/22)
Abstract: A series of novel 1,2,3-triazoles (8a–8m) were synthesized usingclick chemistry in excellent yields and were characterized by IR, NMR, MASSspectroscopy and elemental analysis. The final compounds 8a–8m were assessed for theirantifungal activity. Among the compounds tested 8h, 8i, 8b, and 8e demonstrated potentantifungal activity where as compounds 8j,8d, 8l,and 8f were exhibited good antifungal activityagainst tested fungal strains compared to the reference drug Nystatin.
Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
supporting information, p. 10369 - 10372 (2020/09/16)
A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).
Synthesis, anticancer and antioxidant activities of 7-methoxyisoflavanone and 2,3-diarylchromanones
Kanagalakshmi, Kanagasabai,Premanathan, Mariappan,Priyanka, Ragunathan,Hemalatha, Balasubramanian,Vanangamudi, Arumugasamy
experimental part, p. 2447 - 2452 (2010/07/08)
A convenient, fast and high yielding method for the preparation of 7-methoxyisoflavanone and 2,3-diarylchromanones has been developed by the condensation of benzyl-2-hydroxy-4-alkoxyphenylketone with arylaldehyde/paraformaldehyde in presence of diethylamine, assisted by microwave activation. All the synthesized compounds were screened for anticancer as well as antioxidant activities. Among the nine compounds, 7-methoxyisoflavanone 7 and diarylchromanone 6c shows potential anticancer activity and diarylchromanone 6b has potential antioxidant activity. Compound 6h possesses anticancer and antioxidant activity at the same concentration.
Biocatalytic acylation studies on novel 3-aryl-3-hydroxymethyl-2, 3-dihydro-4H-1-benzopyran-4-ones
Kumar, Vijayendra,Kumar, Rajesh,Raunak,Poonam,Sharma, Sunil K,Prasad, Ashok K,Cholli, Ashok L,Olsen, Carl E,Parmar, Virinder S
, p. 1501 - 1510 (2008/09/19)
(±)-3-Aryl-3-hydroxymethy1-2,3-dihydro-4H-1-benzopyran-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding phenylacetic acid leading to the formation of 2,4-dihydroxyphenyl aryl ketones, which upon monome
Heteroaryl-containing isoflavones as aromatase inhibitors
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Page/Page column 6, (2008/06/13)
Compounds and methods useful for treating and prevention of cancer, particularly hormone-dependent breast cancer. Provided are compounds of formula I: wherein X is selected from O, N, S, SO, SO2, and S(CH2)n, wherein n=1-1
Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones
Kim, Young-Woo,Hackett, John C.,Brueggemeier, Robert W.
, p. 4032 - 4040 (2007/10/03)
Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, we describe the design, synthesis, and biological evaluation of a novel series of 2-(4′-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors.
A convenient one-pot synthesis of 2-(alkylthio)isoflavones from deoxybenzoins using a phase transfer catalyst
Kim, Young-Woo,Brueggemeier, Robert W
, p. 6113 - 6115 (2007/10/03)
A convenient phase transfer catalysis procedure for the synthesis of 2-(alkylthio)isoflavones is described. A number of compounds of potential pharmaceutical interest can be prepared in a single step at ambient conditions from various, easily accessible d
An efficient 'one pot'synthesis of isoflavones
Balasubramanian, Sreenivasan,Nair, Muraleedharan G.
, p. 469 - 484 (2007/10/03)
Initial formation of deoxybenzoin 3 from phenyl acetic acid 1 and phenol 2 in the presence of BF3.Et2O followed by its treatment at room temperature with N, N'-dimethyl (chloromethylene) ammonium chloride, generated by reacting PCl5 with DMF provides a mild and efficient route for a 'one pot' synthesis of Isoflavones in high yields.
The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis
Balasubramanian, Sreenivasan,Ward, Donald L.,Nair, Muraleedharan G.
, p. 567 - 570 (2007/10/03)
The yellow intermediate 4f produced during the reaction of the deoxybenzoin 3f with N,N'-dimethyl(chloromethylene)ammonium chloride in the presence of BF3*Et2O prior to the formation of the corresponding isoflavone was isolated for the first time and characterized by NMR, MS and single-crystal X-ray diffraction techniques. These yellow intermediates showed anticancer, nematicidal and mosquitocidal activities.
Synthesis of 3-aryl-1-(4-methoxyphenyl)-2--2-propen-1-ones and benzopyran derivatives
Verma, Braham S.,Dhindsa, Kuldip Singh,Sangwan, Naresh K.
, p. 239 - 243 (2007/10/02)
Acylation of anisole (5) or m-methoxyphenol (6) with arylacetic acid (7 or 8) gives the corresponding deoxybenzoins (9-12) along with minor isomeric product 13 in one case.Acetylation of 4-hydroxy-4'-methoxydeoxybenzoin (10) with acetic anhydride in pyridine or its alkylation with N-(2-chloroethyl)diethylammonium/pyrrolidinium chloride furnishes the corresponding deoxybenzoin derivatives (14-16).Condensation of 9, 11, 15 and 16 with araldehydes affords the corresponding title compounds 2-propen-1-ones (17, 19 and 21-23). 1-(2-Hydroxy-4-methoxyphenyl)-2,3-diphenyl-2-propen-1-one (19) is isomerized using silica gel or hydrochloric acid to 2,3-trans-2,3-dihydro-7-methoxy-2,3-diphenyl-4H-1-benzopyran-4-one (24) which on sodium borohydride reduction provides a mixture of isomeric benzopyranols (25).Dehydration of 25 gives 7-methoxy-2,3-diphenyl-2H/4H-1-benzopyran (27).The isomeric 7-methoxy-2,4-diphenyl-2H/4H-1-benzopyran (28) is prepared by the reaction of 2,3-dihydro-7-methoxy-2-phenyl-4H-1-benzopyran-4-one (26) with phenylmagnesium bromide.Condensation of 11 with 7 in acetic anhydride/triethylamine furnishes 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one (29).
