Trimethoxy Phenyl Research Articles

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions.

Diaryliodonium(III) salts are versatile reagents that exhibit a range of reactions, both in the presence and absence of metal catalysts. In this study, we developed efficient synthetic methods for the preparation of aryl(TMP)iodonium(III) carboxylates, by reaction of (diacetoxyiodo)arenes or iodosoarenes with 1,3,5-trimethoxybenzene in the presence of a diverse range of organocarboxylic acids. These reactions were conducted under mild conditions using the trimethoxyphenyl (TMP) group as an auxiliary, without the need for additives, excess reagents, or counterion exchange in further steps. These protocols are compatible with a wide range of substituents on (hetero)aryl iodine(III) compounds, including electron-rich, electron-poor, sterically congested, and acid-labile groups, as well as a broad range of aliphatic and aromatic carboxylic acids for the synthesis of diverse aryl(TMP)iodonium(III) carboxylates in high yields. This method allows for the hybridization of complex bioactive and fluorescent-labeled carboxylic acids with diaryliodonium(III) salts.

Synthesis and Biological Activity Screening of Newly Synthesized Trimethoxyphenyl-Based Analogues as Potential Anticancer Agents.

A group of novel trimethoxyphenyl (TMP)-based analogues were synthesized by varying the azalactone ring of 2-(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxybenzylidene)oxazolone 1 and characterized using NMR spectral data as well as elemental microanalyses. All synthesized compounds were screened for their cytotoxic activity utilizing the hepatocellular carcinoma (HepG2) cell line. Compounds 9, 10 and 11 exhibited good cytotoxic potency with IC50 values ranging from 1.38 to 3.21 μM compared to podophyllotoxin (podo) as a reference compound. In addition, compounds 9, 10 and 11 exhibited potent inhibition of β-tubulin polymerization. DNA flow cytometry analysis of compound 9 shows cell cycle disturbance at the G2/M phase and a significant increase in Annexin-V-positive cells compared with the untreated control. Compound 9 was further studied regarding its apoptotic potential in HepG2 cells; it decreased the level of MMP and Bcl-2 as well as boosted the level of p53 and Bax compared with the control HepG2 cells.

Trimethoxyphenyl containing compounds: Synthesis, biological evaluation, nitric oxide release, modeling, histochemical and histopathological studies

Novel series of trimethoxy phenyl containing chalcone 3, 5, 6, 7, pyrazoline 4a&b, 9a-h and pyrazole 10a&b scaffolds were designed and synthesized. They were characterized by spectral data and elemental analyses. All newly synthesized compounds were screened for their in vitro COX-1/COX-2 inhibitory activities and in vivo anti-inflammatory activity. All the target compounds showed COX-2 inhibitory activity over COX-1. Compound 5c was the most active derivative with higher COX-2 inhibitory activity (IC50 = 0.039 µM) than celecoxib (IC50 = 0.045 µM), and selectivity index value of 321.28 nearly equal to that of celecoxib (S.I. = 326.66). Four additional derivatives 5a, 6, 8b and 9f exhibited excellent COX-2 inhibitory activity (IC50 = 0.041 – 0.049 µM) if compared to the reference drug, celecoxib, with selectivity index values (S.I. = 230.61 – 278.05). Additionally, prolonged in vivo A.I activity was observed in compounds 9e, 9 g, 10a and 10b with % inhibition ranged from 33.21 to 44.52%, after 7 h from carrageenan injection. Compound 9e appeared normal without degeneration similar to celecoxib as resulted from histolopathogical study. Compounds containing NO releasing moieties, 7, 10a and 10b were assesses to overcome the gastrointestinal side effects. Molecular modeling study was operated and achieved a parallel correlation with in vitro COX-2 assay results. Pharmacokinetic study for all the prepared compounds was developed.

Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates.

High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.

Synthesis, Characterization and Theoretical Study of Some Transition Metal Complexes with New Schiff Base Derived from 1,2,4-triazole

The present work involves, new Schiff base of (E)-2-(((3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)imino)methyl)phenol (L2) has been synthesized by condensation reaction of 4-amino-5-(3,4,5trimethoxy phenyl)-4H-1,2,4-triazole-3-thiol with 2-hydroxybenzaldehyde. The new Schiff base (L2) used as a ligand to synthesize a new complex with Co(II), Ni(II), Cu(II), Pd(II), and Cd(II) metal ions by 1:1 (Metal: ligand) ratio. New ligand and their complexes have been exanimated and confirmed by fourier-transform infrared (FT-IR), ultraviolet-visible (UV-visible), proton nuclear magnetic resonance (1HNMR), carbon13 nuclear magnetic resonance (13CNMR), microelement analysis (CHNS), thermal analysis (TG-DTA), atomic absorption flame (AAF), conductivity and magnetic susceptibility. The results obtained from spectra, elemental analyses and thermal analyses (TG-DTA) and compare by density functional theory (DFT) and TD-DFT calculations were screened for some selected complexes and the observed data indicated their stability and the expected chemical formula, palladium(II) were square planner geometry in [PdL2Cl] formula, whereas the copper(II) , cobalt (II), Nickel (II), and cadmium (II) were octahedral and tetrahedral geometry respectively in the formulas, [ML2(H2O)2Cl] and [CdL2Cl] , M=Cu, Ni and Co(II) ions.

Design, synthesis, anticancer evaluation and molecular docking studies of chalcone linked pyrido[4,3-b]pyrazin-5(6H)-one derivatives

A series of novel chalcone derivatives pyrido[4,3-b]pyrazin-5(6H)-one (10a-j) were designed, synthesized and their structures were confirmed by 1H NMR, 13C NMR and mass spectral data. Further, all derivatives were tested for their anticancer activities against five human cancer cell lines such as MCF-7 (breast cancer), A-549 (lung cancer), Colo-205 (colon cancer), A2780 (ovarian cancer) and DU-145 (prostate cancer) by employing MTT assay. The clinically used drug etoposide was used as standard reference and the anticancer activity was expressed as the IC50 in µM. Among the ten compounds examined compounds, 10b, 10c, 10d, 10h, and 10i possessed more promising anticancer activity. A molecular docking study implying ATR kinase was carried out to observe the binding mode of chalcone derivatives pyrido[4,3-b]pyrazin-5(6H)-one (10a-j) on the active site of ATR kinase. The most promising compound, 10h showed π−π stacking interaction of trimethoxy phenyl and pyridone moiety with the residue Trp850, while the carbonyl (α,β-unsaturated carbonyl) and methoxy functions showed H-bond interaction with the residue Ser773 and Thr856 respectively.

Synthesis and biological evaluation of oxazinonaphthalene-3-one derivatives as potential anticancer agents and tubulin inhibitors.

Objective(s): In the present study, a new series of oxazinonaphthalene-3-one analogs was designed and synthesized as novel tubulin inhibitors.Materials and Methods:The cytotoxic activity of the synthesized compounds was evaluated against four human cancer cell lines including A2780 (human ovarian carcinoma), A2780/RCIS (cisplatin resistant human ovarian carcinoma), MCF-7 (human breast cancer cells), and MCF-7/MX (mitoxantrone resistant human breast cancer cells), those compounds which demonstrated the most antiproliferative activity in the MTT test were selected to investigate their tubulin inhibition activity and their effects on cell cycle arrest (at the G2/M phase). Moreover, molecular docking studies of the selected compounds in the catalytic site of tubulin (PDB ID: 4O2B) were carried out to describe the results of biological experiments.Results:Most of our compounds exhibited significant to moderate cytotoxic activity against four human cancer cell lines. Among them, Compounds 4d, 5c, and 5g, possessing trimethoxy phenyl, showed the most antiproliferative activity with IC50 values ranging from 4.47 to 52.8 μM.Conclusion:The flow cytometric analysis of A2780 cancer cell line treated with compounds 4d, 5c, and 5g showed that these compounds induced cell cycle arrest at the G2/M phase. Compound 5g, the most antiproliferative compound, inhibited tubulin polymerization in a dose-dependent manner. Molecular docking studies of 5g into the colchicine-binding site of tubulin displayed a possible mode of interaction between this compound and tubulin.

Corrigendum: Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers

Corrigendum: Trimethoxyphenyl (TMP) as a Useful Auxiliary for <i>in situ</i> Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers

Discovery Of Novel Sulphamidopyrimidine Derivatives As Novel Brd4 And Cox2 Inhibitors In Cancer And Inflammation – Synthesis, Structure – Activity Relationship And In-Vitro Efficacy

A pharmacophoric filtering strategy was applied using Accelerys Discovery studio 3.5 by aiming the objectives to discover a series of novel sulphamidopyrimidine derivatives as potent dual inhibitors of BRD4 and COX2. The designed sulphamidopyrimidine derivatives were subjected to various in-silico studies such as docking, ADME and toxicity studies. The best compounds from the virtual studies were selected for synthesis and were synthesized from various substituted aromatic aminopyrimidine derivatives and sulphonamide derivatives in the presence of base. The synthesized compounds were characterized by FTIR, 1H NMR and Mass spectral data. Herein we performed the in-vitro cytotoxicity assay in four different cell lines such as PA-1, MCF-7, MG-63, HeLa and enzyme inhibition (BRD4 & COX2) studies also. The sulphamidopyimidine derivatives such as 3ce, 3be and 3aa which possess substituents such as 3, 4, 5 trimethoxy phenyl, furfuryl, 4 nitro phenyl and indolyl were found to exhibit better cytotoxicity with IC50 in the range of ˃50µM and enzyme inhibitory activity with a percentage inhibition in the range of 75-80% COX-2 inhibition and 40-50% BRD4 inhibition. From the results it was indicated that the synthesized sulphamidopyrimidine derivatives might serve as a tool for the development of dual inhibitors of BRD4 & COX2 for the potential treatment of cancer and inflammation.

Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers

AbstractHerein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way, aryl iodides are used as reagents in a metal‐free reaction with phenols, and a trimethoxyphenyl (TMP) group is used as a “dummy” group to facilitate transfer of a wide range of aryl moieties. The scope of aryl electrophiles and phenol nucleophiles is broad (&gt;30 examples) and the yields are high (52–95%, 80% avg.). One‐pot coupling reactions avoid the synthesis of diaryliodonium salts and provide opportunities for sequential reactions and novel chemoselectivity.magnified image

Design and synthesis of novel parabanic acid derivatives as anticonvulsants.

In this work a set of novel derivatives of parabanic acid 9a-d, 12a-d and 13a-d was synthesized and their anticonvulsant potential was evaluated. All the compounds under investigation exhibited anticonvulsant activity in both scPTZ and MES tests. In phase II anticonvulsant study, the trimethoxy phenyl derivative 9a evoked the highest potency among the tested compounds in scPTZ test. It displayed 1.72- and 17.05-folds activity more than the standard drugs phenobarbital and ethosuximide, respectively. In addition, the margin of safety for compound 9a is better than that of the reference antiepileptic drug ethosuximide. Also, compound 9a was devoid of hepatotoxicity indicated by measurements of serum level of ALT, AST, ALP, albumin and total protein. Furthermore, treatment with compound 9a significantly increased the GABA brain level by 2.56-folds compared to the control value. Additionally, molecular docking was performed on the active site of GABA-AT to clarify the interactions of the most potent compound 9a with the enzyme. In MES test, compound 12a exhibited the most potent activity against electric stimuli-induced seizures with the lowest ED50=13.7mg/kg and protective index>36.5. Both candidates 9a and 12a could be a good starting point to develop new molecules as novel antiepileptic drugs.

Colchicine-like β-acetamidoketones as inhibitors of microtubule polymerization: Design, synthesis and biological evaluation of in vitro anticancer activity.

Objective(s):In this study a series of novel colchicine-like β-acetamidoketones was designed and synthesized as potential tubulin inhibitorsMaterials and Methods:The cytotoxicity of the novel synthesized β-acetamidoketones was assessed against two cancerous cell lines including MCF-7 (human breast cancer cells) and A549 (adenocarcinomic human alveolar basal epithelial cells) employing the MTT test. Tubulin polymerization test was done by using a commercial kit (tubulin polymerization assay kit).Results:In general, the cytotoxicity activities were highly dependent on the aromatic substitution pattern of phenyl ring at β position of β-acetamidoketones. Based upon, compound 4f possessing the same structural elements of colchicine and chalcone 1, revealed the most cytotoxicity more than the other β-acetamidoketone against the cancerous cell lines and showed moderate antitubulin effect. The tubulin inhibitory effect of 4f, colchicine and chalcone 1 were consistent with their antiproliferative activities. Molecular docking studies of 4f, into the colchicine-binding site of tubulin exhibited possible mode of interaction between this compound and tubulin.Conclusion:The structure activity relationship (SAR) data attained showed that the presence of trimethoxy phenyl attached to carbonyl group of β-acetamidoketones and a methoxy group at para position of the other ring are essential for cytotoxic activity. In general, the cytotoxicity activities were highly dependent on the aromatic substitution pattern of phenyl ring at β position of β-acetamidoketones.

Effect of increasing methoxyphenyl substitution on pyrene pyrazoline enduring green light emitting materials

The pyrene pyrazoline derivatives containing mono, di and tri methoxy phenyl substituents were synthesized. Thermal stability and glass transition temperatures changed with progressive substitution of methoxy phenyl group. X-Ray Diffraction pattern revealed their crystalline nature. The photophysical properties of materials exhibited green emission at 510 nm (PP1My), 510 nm (PP2My) and 508 nm (PP3My) in solution and yellow emission at 580 nm (PP1My), 574 nm (PP2My) and 563 nm (PP3My) in solid state. The blue shift in the emission in solid state was owing to aggregation induced by methoxy substituent. The color chromaticity values were calculated for their color purity of green and yellow emissions. Ten different solvents were used to examine solvatochromism and red shifted emission observed in enhancing polarity of solvents and dual emission in cyclohexane were suggested twisted conformation of molecule that led to Intramolecular charge transfer becomes twisted Intramolecular charge transfer. Nonlinear optical properties of pyrazoline derivatives improved when electron donates methoxy groups and polyaromatic luminophore of pyrene were substituted on pyrazoline moiety. The third order nonlinear optical properties were investigated by Z-scan technique at 532 nm and exhibited strong reverse saturable absorption and self-defocusing natures. The optimized geometry evidences that molecules have twisted structures and looks like an antenna molecules. These kinds of molecules are demand in energy applications such as light harvesting solar materials and light emitting materials.

Synthesis, Anticancer Screening and Molecular Docking Studies of New Heterocycles with Trimethoxyphenyl Scaffold as Combretastatin Analogues.

In this study, synthesis, molecular docking and anticancer screening of new series of substituted heterocycles with trimethoxy phenyl scaffold as Combretastatin analogues were described. Substituted pyridines were synthesized via the reaction of (E)-3-(dimethylamino)-1-(3,4,5- trimethoxyphenyl)prop-2-en-1-one (2) with active methylene reagents. Substituted pyrimidines were prepared by the reaction of the enaminone (2) with heterocyclic amines and 6-amino thiouracil. Furthermore, a series of pyrazoles substituted with trimethoxyphenyl scaffold were prepared by the reaction of the enaminone 2, with selected examples of hydrazonoyl halides. The cytotoxic effect of the newly compounds was evaluated against HePG-2, HCT-116, MCF-7 and PC3 cancer cell lines. Among the new products, compounds 2, 3, 7 and 10 were found to exhibit promising results as anticancer agents. The IC50 values of 2, 3 and 7 were 54.6, 77.4 and 47.4 on PC3 respectively. Also, compound 2 had IC50 28.06 on MCF7. Moreover, the selectivity index indicated that compounds 2 and 3 are safe.

One-Pot Synthesis of Unsymmetric Diaryliodonium Salts from Iodine and Arenes.

The first synthesis of unsymmetric diaryliodonium salts directly from iodine and arenes is presented. The methodology provides diaryliodonium salts with the trimethoxyphenyl (TMP) moiety as dummy group. The protocol avoids the customary use of iodoarenes, which can be both expensive and toxic. Excess reagents are not required, and the reactions are performed under mild conditions. O-Arylations with these TMP salts were demonstrated to be highly chemoselective.

Abstract 1664: New moieties mimicking the trimethoxyphenyl (ring A) of combretastatin A-4: Synthesis and biological evaluation

Abstract Combretastatin A-4 (CA-4), its phosphate disodium (CA-4P) and serine hydrochloride salts (AVE8062) are part of a new class of anticancer agent named vascular disrupting agent (VDA). In addition to act as potent antimicrotubule agents in cancer cells, these drugs have the ability to target and disrupt the cytoskeleton of neo-endothelial vascular cells leading to selective and rapid shutdown of blood flow through tumors. The recent success of CA-4 salts in preclinical studies and its achievement in clinical studies prompted the comprehensive study of the structure-activity relationships related to CA-4. Several thousand derivatives and analogs were synthesised and biologically evaluated by modifying the ring B and the ethenyl bridge of CA-4; only few studies have been done on the trimethoxyphenyl (TMP) ring A since it had been previously found crucial for anticancer potency. In the course of our own structure-activity relationship studies, we recently reported two new families of antimicrotubule agents where the ethenyl bridge of CA-4 was substituted by a sulfonate group and the TMP was replaced either by a phenylimidazolidin-2-one (IMZ) or phenylchloroethylurea (CEU) moieties. IMZs are potent antiproliferative agents exhibiting IC50 in the nanomolar range while CEU are soft alkylating agent normally active in micromolar range. IMZ and CEU arrest the cell cycle in G2/M phase, bind to the colchicine-binding site (C-BS) on β-tubulin leading to the disruption of the cytoskeleton and apoptosis. Although the structure-activity relationship studies of IMZ and CEU derivatives suggest that they mimic the TMP moiety of CA-4, molecular modeling experiments show that IMZs replace the ring B of CA-4 instead of ring A. In this context, we synthesized 3 series of CEU and IMZ where the sulfonate bridge was replaced by an ethenyl bridge to confirm that IMZ and CEU mimic the TMP moiety of CA-4. First, IMZ and CEU analogs to CA-4 exhibited antiproliferative activities in nanomolar range and in micromolar range, respectively as their parent compounds. Moreover, the most potent compounds blocked the cell cycle progression in G2/M-phase, disrupted the cytoskeleton and bind also the C-BS. Our results strongly suggest that IMZ and CEU mimic the TMP (ring A) of CA-4. These two moieties could be used as bioisosteric equivalents to circumvent some problems that might be encountered during the clinical development of CA-4. In addition, they could be used also to replace the TMP moiety found in several other antimitotics such colchicine, podophyllotoxin and steganacin to design new potent antimicrotubule agents. Citation Format: Mathieu Gagné-Boulet, Sébastien Fortin, Jacques Lacroix, Carole-Anne Lefebvre, Marie-France Côté, René C-Gaudreault. New moieties mimicking the trimethoxyphenyl (ring A) of combretastatin A-4: Synthesis and biological evaluation. [abstract]. In: Proceedings of the 106th Annual Meeting of the American Association for Cancer Research; 2015 Apr 18-22; Philadelphia, PA. Philadelphia (PA): AACR; Cancer Res 2015;75(15 Suppl):Abstract nr 1664. doi:10.1158/1538-7445.AM2015-1664

Comparison of crystal structures of 4-(benzo[b]thio-phen-2-yl)-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole and 4-(benzo[b]thio-phen-2-yl)-2-methyl-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole.

The title compound, C19H17N3O3S (I), was prepared by a [3+2]cyclo-addition azide condensation reaction using sodium azide and l-proline as a Lewis base catalyst. N-Methyl-ation of compound (I) using CH3I gave compound (II), C20H19N3O3S. The benzo-thio-phene ring systems in (I) and (II) are almost planar, with r.m.s deviations from the mean plane = 0.0205 (14) in (I) and 0.016 (2) Å in (II). In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzo-thio-phene ring systems. The trimeth-oxy phenyl rings make dihedral angles with the benzo-thio-phene rings of 38.48 (4) in (I) and 60.43 (5)° in (II). In the crystal of (I), the mol-ecules are linked into chains by N-H⋯O hydrogen bonds with R (2) 1(5) ring motifs. After the N-methyl-ation of structure (I), no hydrogen-bonding inter-actions were observed for structure (II). The crystal structure of (II) has a minor component of disorder that corresponds to a 180° flip of the benzo-thio-phene ring system [occupancy ratio 0.9363 (14):0.0637 (14)].

Solvent Effect on the Fluorescence Properties of Two Biologically Active Thiophene Carboxamido Molecules

The absorption and fluorescence spectra of two thiophene carboxamido molecules namely 2–( - trimethoxy phenyl) imino–3–N–ethylcarboxamido–4, 5, tetramethylene thiophene (X) and 2-( -N, N-dimethylaminophenyl) imino-3-(N- methylphenyl carboxamido)-4, 5, tetramethylene thiophene (Y) have been recorded at room temperature. The ground (mg) and excited (me) state dipole moments are estimated from Lippert, Bakhshiev, Kawski-Chamma-Viallet equations by using the variation of Stokes shift with microscopic solvent dielectric constant (e) and refractive index (n). The excited dipole moments were also estimated by using the variation of Stokes shift with microscopic empirical solvent polarity parameter and the values are compared. It was estimated that dipole moments of the excited state were higher than those of the ground state of both the molecules. Further, the change in dipole moment (Dm) were calculated both from solvatochromic shift method and on the basis of microscopic empirical solvent polarity parameter .

Synthesis of 1,2,3-triazole tethered bifunctional hybrids by click chemistry and their cytotoxic studies

In view of the drug resistance with most of the currently used anticancer drugs, molecular hybrids of pyrazolyl chalcones and p-nitro benzyl functionalities tethered by triazole ring have been synthesised and evaluated for cytotoxic studies against three human cancer cell lines (THP, COLO-205, A-549). The results of the preliminary investigation exhibited marked dependence of the cytotoxic activity on the electronic factors. Placement of naphthyl (JGPT-11) and trimethoxy phenyl ring (JGPT-6) as ring A proved to be extremely beneficial in enhancing the cytotoxic potential. Thus we herein report the synthesis and cytotoxic studies of a new class of molecular hybrids. Detailed investigation on the biological mechanistic insights of JGPT-11 and 6 is under progress.

Anticancer efficacy of phenolics based structurally related compounds and their radical scavenging action

AbstractCancer, one of the leading causes of death worldwide, is an abnormal cell proliferation that fails to respond to the normal signals. In an effort to eradicate the growing menace of cancer, a clear understanding of fundamental biology and molecular mechanism of carcinogenesis is essential for targeted therapies. Among the devised strategies in use for cancer treatment, the one that is of immense interest is the development of plant based novel anticancer agents. Due to their tremendous availability, biological activity and efficacy, the phytochemicals deemed a gibbous future in chemoprevention. In the present study, several phenolics based structurally related compounds of steroidal and non-steroidal skeleton were synthesized and tested for their modulatory effect on ornithine decarboxylase activity, an enzyme highly upregulated in cancer. Additionally, these compounds were also examined for radical scavenging extent to establish a correlation with the anticancer property. Our result suggests that the tested compounds possessed radical scavenging activity, for being the inherent property of the phenolics. 3-(3’,4’5’-trimethoxyphenyl)-4,5,6-trimethoxyindan-1-one oxime exhibited highest inhibition of enzyme activity (91%) followed by 1-(2,4-dibromophenyl)-3-[3-methoxyestra 1,3,5(10)-trien-17-acetate,2-yl]-2-propen-1-one (85%), 2-Hydroxy, 3-(3’,4’,5’-trimethoxy phenyl)-4,5,6-trimethoxy ind-2-en-1-one (80%), 1-(3,4-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one (74%) and 1-(3,-methoxy, 4-hydroxyphenyl)-3-[3-methoxyestra 1,3,5(10)-trien-17-acetate, 2-yl]-2-propen-1-one (67%). Furthermore, it was observed that 1-(3-Methoxy, 4- hydroxyphenyl)-3-[3-methoxyestra 1,3,5 (10)-trien-17-acetate, 2-yl]-2-propen-1-one showed the highest scavenging effect (67%) in nitric oxide assay, whereas 1-(3-methylphenyl)-3-[3-methoxy, 17-hydroxyestra 1,3,5(10)-trien, 2-yl]-2-propen-1-one showed maximum inhibition of radical formation in 2,2-diphenyl-1-picrylhydrazyl analysis. Most of these compounds possessed a 3,4,5-trimethoxyphenyl unit which might be inducing enzyme inhibition and scavenging radical formation. Further investigations are on the way to establish the structure-activity relationship, so that these compounds can be developed as anticancer agents.