Synthesis and Characterization of N-N-{Bis(2′-Chloroethylamino)- Nitroso}-2-Benzylidene-1-Benzofuran Derivatives as Antileukemic Agents (original) (raw)
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Synthesis, Characterization, and Biological Activities of New Benzofuran Derivatives
Heterocycles, 2007
A number of new benzofuran derivatives, ethyl 3-[(alkylamino)methyl]-6-methoxy-1-benzofuran-2-carboxylates (5a-i), were obtained via the reaction between ethyl 3-(bromomethyl)-6-methoxy-1-benzofuran-2-carboxylate (3) and amines or amino acid ethyl esters. In addition, 1,4-bis[(ethyl 6-methoxy-1benzofuran-3-yl-2-carboxylate)methyl]piperazine (9), N, N'-diethyl-N,N'-bis[(6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]but-2-ene-1,4-diamine (10) and 1,2-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]-1,2-dimethylhydrazine (11) were also obtained from the reaction of 3 with diamines. Their in vitro anti-HIV-1 (strain III B ) and HIV-2 (strain ROD) activities of the synthesized compounds in human T-lymphocyte were tested; ethyl 3-bromomethyl-6methoxycoumarlate displayed an ability to inhibit HIV-1 and HIV-2 replication in cell culture at non-toxic concentrations.
International Journal of Organic Chemistry, 2012
Substituted 2-benzylidene-1-benzofuran-3-ones are commonly known as aurones. This class of bioactive heterocycles belongs to flavonoid family. The article intends to put forth the rational design and synthesis of a new series of aurones using 3',5'-dibromo-2',4'-dihydroxychalcones and copper bromide in presence of DMF-water mixture (8:2, v/v) for the first time. Preliminary bioassay shows that most of compounds have good trypanocidal activity against Trypanosoma cruzi at 10 μg/mL. Few compounds are equally potent to the standard drugs Benznidazole and Nifurtimox. The structures of the newly synthesized products 2a-n were established by elemental analysis, FTIR, 1 H NMR, 13 C NMR and mass spectroscopic studies.
Synthesis of potent antitumor and antiviral benzofuran derivatives
Bioorganic & Medicinal Chemistry Letters, 2009
Cytotoxicity Antiviral activity HIV and HIV-1 RT inhibitory activity HCV NS3-4A protease inhibitor activity a b s t r a c t A new series of potent antitumor and antiviral benzofuran derivatives was synthesized by the reaction of the furochromone-6-carboxaldehydes 1 and 2 with different heterocyclic amines to yield the benzofuran-5-carbonyl derivatives 4-11. The synthesized compounds 1, 3-11 were tested against twelve different human cancer cell lines and all of the compounds were more potent than the comparative standards. The HIV inhibitory activity of the tested compounds 1, 3-11 showed that they have higher potency than Atevirdine. Moreover, compound 6 was significantly potent with wider therapeutic index. The HIV-1 RT inhibitory activity showed that compounds 10, 11, 3 and 4 were notably potent but with lower therapeutic index than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that they have weaker potency and less therapeutic index than VX-950, although compounds 1, 4, 9 and 6, respectively exhibited significant activity.
Medicinal Chemistry Research, 2015
Two new series of aurone compounds were synthesized via an oxidative cyclization reaction of 2 0 -hydroxy-chalcones. Series (A) consists of 1a-3a aurones with different substitutions on a B-ring at position 4 0 , and series (B) is made up of 1b-3b aurones that have different substitutions at position 2 0 of a B-ring. Structures of the synthesized compounds were characterized and confirmed by FTIR (1D and 2D NMR) and EI mass spectral studies. The molecular structure of 2b was further confirmed by the X-ray crystallographic technique, with the compound found to be in Z-isomeric form. The compounds of both series were tested for their antiproliferative activity against human colorectal tumor (HCT 116), human chronic myelogenous leukemia (K562) and hormone-dependent breast cancer (MCF-7) cell lines according to an MTT assay. Series (B) exhibited a higher cytotoxic effect on the cancer cell lines compared to series (A). Selectively, the most promising results have been shown by the two most active compounds, 1b (Z-5,7, 2 0 -trichloro-aurone), which resulted in IC 50 values of 36, 23 and 23 lM against HCT 116, MCF-7 and K562 cancer cells, respectively. Compound 3a (Z-5, 7-dichloro-4 0 -methyl-aurone) exhibited the highest activity against the K562 cell line (IC 50 = 20 lM), which can be compared to that of the standard drug, betulinic acid, with an IC 50 value of 15 lM. The results of the present study suggested that aurone derivatives emerged as a potential candidate for the development of future chemotherapeutic agents.
European Journal of Medicinal Chemistry, 2010
Base catalyzed condensation of enaminoketones (3a,b) with malononitrile yields the respective 7-imino-5[2(substituted)prop-1-enyl]furochromene-6-carbonitriles (4a-d) according to the nature of base used. Compounds (3a, b) condense also with indan-1,3diketone (5) to give alpha, beta-unsaturated carbonyl compounds (6a) and (6b), respectively. Pyrrolidine-catalyzed condensation of visnaginone (2a) and khellinone (2b) with active methylenes yields the corresponding 1-[7,7-(substituted) furobenzodihydropyrone derivatives (7a-e) which condense with semicarbazide to give the respective semicarbazones (8a-e). Compounds (8b,e) react with thionyl chloride to give the respective 1,2,3thiadiazoles (9a,b) meanwhile compounds (8a-e) react also with selenium dioxide to give 1,2,3-selenadiazoles (9c-g), respectively. Chalcones (11a,b) were obtained upon condensing (2a,b) with ferrocene-2-carboxaldehyde (10). Compatible elementary and spectroscopic measurements were in good accord with the structures postulated for the new compounds. The antitumor activities of certain selected new compounds were screened, in vitro, against a panel of four (breast: MCF-7, cervix: HELA, colon: HCT116 and liver: HEPG2) human solid tumor cell lines and the structure activity relationship (SAR) was discussed.
European Journal of Medicinal Chemistry, 2013
In this manuscript the synthesis and biological activity of novel heterocyclic derivatives of benzofuran-2carboxamides 3aej and 6aef is presented. Biological evaluation in vitro revealed that only few compounds exerted concentration-depended antiproliferative effects on tumour cell lines at micromolar concentrations. In particular, 2-imidazolynyl substituted compound 6f showed selectivity on SK-BR-3 cell line while 2-N-acetamidopyridyl substituted 3h and 2-imidazolynyl substituted amide 3i showed selective concentration-dependent antiproliferative effects on SW620 cell line. Compounds 3h and 6f induced apoptosis while compound 3i acted through a cell death mechanism other than apoptosis. European Journal of Medicinal Chemistry 59 (2013) 111e119 d ¼ 9.94 (brs, 2H, NH imidazolynyl ), 8.84 (s, 1H, NH amide ), 8.61 (d, 1H, J ¼ 2.46 Hz, H arom. ), 7.94 (dd, 2H, J 1 ¼ 8.88 Hz, J 2 ¼ 2.58 Hz, H arom. ), 7.74 (d, 1H, J ¼ 7.74 Hz, H arom. ), 7.62 (dd, 1H, J 1 ¼ 8.34 Hz, J 2 ¼ 0.98 Hz, H arom. ), 7.53 (d, 1H, J ¼ 1.12 Hz, H arom. ), 7.43 (dt, 1H, J 1 ¼ 8.46 Hz, J 2 ¼ 1.32 Hz, H arom. ), 7.31 (dt, 1H, J 1 ¼ 7.92 Hz, J 2 ¼ 0.98 Hz, H arom. ), 3.87 (s, 4H, CH 2 ); 13 C NMR (75 MHz, DMSO-d 6 ): d (d), 106.0 (s), 45.6 (t, 2C); UV (EtOH) l max /nm ¼ 322; elemental analysis calcd. (%) for C 17 H 15 N 4 O 2 Cl: C 59.57, H 4.41, N 16.34; found C 59.68, H 4.60, N 16.62. DMSO-d 6 ): d ¼ 13.63 (s, 1H, NH amide ), 9.11 (s, 1H, H arom. ), 8.31 (dd, 1H, J 1 ¼ 8.88 Hz, J 2 ¼ 1.20 Hz, H arom. ), 8.24 (s, 1H, H arom. ), 7.97 (d, 1H, J ¼ 8.76 Hz, H arom. ), 7.89 (d, 1H, J ¼ 7.88 Hz, H arom. ), 7.76 (d, 1H, J ¼ 8.46 Hz, H arom. ), 7.55 (t, 1H, J ¼ 7.76 Hz, H arom. ), 7.39 (t, 1H, J ¼ 7.56 Hz, H arom. ); 13 C NMR (150 MHz, DMSO-d 6 ): d ¼ 164.2 (s), 155.6 (s), 154.7 (s), 153.8 (s
2016
Background: Aurones are naturally occurring compounds that belong to flavenoids family and have antiplasmodial effects. This study investigated some new aurones derivatives against chloroquine sensitive Plasmodium falciparum. Here we report the synthesis, in vitro antiplasmodial activity and cytotoxic evaluation of 11 compound from derivatives of (Z)-2- benzylidene-4, 6-dimethoxybenzofuran-3(2H)-one. Methods: The cytotoxic evaluations of active compounds were performed with MTT (3-[4, 5-dimethylthiazol-2-yl]-2, 5 diphenyltetrazolium bromide) assay on human breast cancer cell lines; MCF7 and T47D. Results: From 11 compounds M3, M6 and M7 compounds showed good anti-plasmodial effect against chloroquine-sensitive 3D strain of P. falciparum with IC50 (50% inhibitory concentration) values of 7.82, 7.27 and 2.3 μM respectively. No noticeable toxicity was observed with these compounds when tested against tested cell lines. Conclusion: The replacement of the 4 and 5 positions at ring B of a...
SYNTHESIS OF A BIOLOGICALLY PERTINENT MOLECULE, AURONES –AN EXTENSIVE REVIEW
Method 2: Few milligram of Copper (II) Bromide in Dimethyl sulfoxide and 2-hydroxychalcones is reflexed SJIF Impact Factor 2.062 ABSTRACT Aurones and its derivatives constitute a class of heterocyclic compounds which add a new dimension in drug development containing benzofuranone molecule. Aurones have been isolated from various natural sources and have been reported for their potent Anticancer, antidiabetic, anti-inflammatory activities Chemists were inspired by the unique properties of Aurones to develop various derivatives of aurone and assess their potential biological pertinence. In this review we have compiled and discussed several methods by which aurones and its derivatives can be chemically synthesized, in an effort to pave the way for a medicinal chemist for a comprehensive and target oriented information for development in this promising area of research.
Recent advantages in benzofurans
Journal of Pharmacognosy and Phytochemistry, 2019
Benzofuran as an important heterocyclic compound is extensively found in natural products as well as synthetic materials. Since benzofuran drivatives display a diverse array of pharmacological activities, an interest in developing new biologically active agents from benzofuran is still under consideration. This review highlights recent findings on biological activities of benzofuran derivatives as antimicrobial and antibreast cancer agents and lays emphasis on the importance of benzofurans as a major source for drug design and development.