Microwave-assisted synthesis of (E)-7-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-(3-arylacryloyl)-4-methyl-2H-chromen-2-ones and their antimicrobial activity

Ashok Dongamanti; Vijaya Lakshmi Bommidi; Ganesh Arram; Ravi Sidda

doi:10.1515/hc-2014-0102

Article Open Access

Microwave-assisted synthesis of (E)-7-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-(3-arylacryloyl)-4-methyl-2H-chromen-2-ones and their antimicrobial activity

Ashok Dongamanti , Vijaya Lakshmi Bommidi , Ganesh Arram and Ravi Sidda

Published/Copyright: October 2, 2014

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From the journal Heterocyclic Communications Volume 20 Issue 5

Abstract

Hybrid compounds are relevant products in the structure-activity relationships analysis. A new series of hybrid compounds containing coumarin, 1,2,3-triazole, and chalcone substructures were synthesized and screened for their antimicrobial activity. The structures of the synthesized compounds have been established on the basis of analytical and spectral data.

Keywords: alkyne; azide; chalcone; click chemistry; 1,3-dipolar cycloaddition; triazole

Introduction

Heterocyclic compounds containing nitrogen and oxygen atoms play an important role in agrochemical and pharmaceutical sciences. A large volume of research has been carried out on triazoles and their derivatives, which has proven the pharmacological importance of this heterocyclic system. 1,2,3-Triazole and its derivatives have received considerable attention in the past few decades due to their chemotherapeutical value. For example, (1-benzyl-1H-1,2,3-triazol-4-yl)methanol and 2-(1-(2-methylbutyl)-1H-1,2,3-triazol-4-yl)propan-2-ol, shown in Figure 1, are potent antimicrobial agents [1]. Other 1,2,3 triazole derivatives exhibit anti-inflammatory, analgesic, local anesthetic, antiallergic, antineoplastic, antimalarial [2], anti-HIV [3], and anticancer activities [4]. 1,2,3-Triazole compounds have also been widely used as synthetic intermediates, dyes, anti corrosive agents, photo stabilizers, photographic materials, and agrochemicals [5].

Figure 1

Representative examples of biologically active triazoles, chalcones, and coumarins and a general structure of synthesized coumarin-chalcone-triazole hybrids.

Coumarins are important oxygen-containing fused heterocycles used in drugs and dyes [6, 7]. The interesting biological activities of coumarins make them attractive targets in organic synthesis. Natural coumarins are known to have antidiabetic activity [8] and are antioxidant, hepato-protective, antimicrobial, antioxidant, anticancer [9], and antiviral agents. Synthetic coumarins are of pharmaceutical importance. The potent antibiotic novobiocin, shown in Figure 1, is a coumarin derivative [10]. These pharmacological properties of coumarin aroused our interest in synthesizing some coumarin derivatives with the aim of testing their microbiological activity. The compounds with the backbone of chalcones have been reported to possess various biological activities such as antimicrobial, anti-inflammatory, analgesic, antiplatelet, antiulcerative, antimalarial, anticancer [11], antiviral, antileishmanial, antioxidant [12], antitubercular [13], antihyperglycemic, and immunomodulatory properties. They show inhibition of chemical mediators release [14], inhibition of leukotriene B4 [15], inhibition of tyrosinase [16], and inhibition of aldose reductase [17]. Other derivatives show estrogenic activities [18]. Licochalcone (Figure 1) exhibits antimalarial activity [19]. Chalcones have also been used as starting materials for the synthesis of various chemicals, including plastics, resins, pesticides, dyes, and pharmaceuticals [20].

Microwave irradiation (MWI) is used for a variety of organic syntheses due to short reaction time, easy workup, and good yields. The microwave oven procedure is now well established in MORE chemistry [21].

Encouraged by the biological importance of coumarins, triazoles, and chalcones, in this report, we describe the synthesis of (E)-7-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-arylacryloyl]-4-methyl-2H-chromen-2-ones 6 by conventional and MWI methods (Scheme 1). The products were evaluated for antimicrobial activity.

Scheme 1

Results and discussion

Chemistry

Herein, we wish to report an efficient, practical, and high-yielding method for the synthesis of compounds 6a–i. The starting material 8-acetyl-7-hydroxy-4-methylcoumarin (1) was prepared by acetylation of 7-hydroxy-4-methylcoumarin followed by rearrangement of the resultant 7-acetoxy derivative. The synthesis of the desired products 6a–i was accomplished by two synthetic strategies shown in Scheme 1. In the first route, compound 2, prepared by propargylation of 1, was subjected to the click reaction with benzyl azide using MWI to give compound 3 [22]. Subsequent condensation reactions of 3 with aryl aldehydes in the presence of piperidine under MWI conditions gave compounds 6a–i in excellent yields. In the second route, the chalcones 4a–i were synthesized first by the reactions of compound 1 with aryl aldehydes in the presence of piperidine under MWI conditions. Propargylation of chalcones 4a–i followed by the click reactions of the resultant intermediate products 5a–i [23] gave the desired products 6a–i. The optimized click reactions were conducted in t-BuOH/water (1:1) in the presence of CuSO4·5H₂O and sodium ascorbate under MWI conditions. In both routes, the use of MWI conditions in each particular step proved to be superior in terms of shorter reaction times and yields of products in comparison to the use of conventional conditions. The final steps of the synthesis of products 6a–i under the two conditions are summarized in Table 1. Structures of all compounds 6a–i were rigorously characterized by IR, ¹H NMR, ¹³C NMR, and MS (Scheme 1).

Table 1

Comparison of yields of compounds 6a–i synthesized under conventional and MWI conditions.

Compound	Yield (%)
	Route 1		Route 2
	Conventional	MWI	Conventional	MWI
6a	75	94	50	65
6b	80	95	40	58
6c	82	96	40	60
6d	79	96	45	55
6e	75	88	50	60
6f	70	90	40	55
6g	75	85	30	40
6h	74	85	40	55
6i	72	85	50	65

Antimicrobial activity

All compounds 6a–i show antimicrobial activity (Table 2 and Figure 2). Importantly, derivatives 6c and 6d exhibit excellent activities against the selected bacterial strains that are superior to the activities of the reference antibiotic amoxicillin. Compounds 6b, 6e, and 6h display good antibacterial activity, and compounds 6f and 6g are moderately active. The coumarin containing triazole derivatives 6a and 6i are weakly active in the antibacterial assay. Compounds 6c,d are also more active against selected fungi that the reference drug mycostatin (Table 2 and Figure 3).

Table 2

Antimicrobial activity of compounds 6a–i.

Compound	Zone of inhibition (mm)
	Gram-positive bacteria		Gram-negative bacteria		Fungi		F. oxysporum
	S. aureus	B. subtilis	E. coli	P. aeruginosa	A. niger	P. italicum	F. oxysporum
6a	11	08	10	04	08	14	17
6b	28	11	28	09	11	18	23
6c	32	13	31	11	13	21	27
6d	35	15	33	14	16	24	30
6e	27	11	27	10	10	19	24
6f	22	09	23	09	09	17	18
6g	20	08	22	07	08	16	19
6h	25	10	23	08	10	16	20
6i	17	06	14	07	09	17	18
Amoxicillin	30	12	30	10	–	–	–
Mycostatin	–	–	–	–	12	20	25

Figure 2

Antibacterial activity of compounds 6a–i.

Figure 3

Antifungal activity of compounds 6a–i.

Conclusions

An efficient microwave synthesis of 1,2,3-triazole derivatives was carried out successfully under mild reaction conditions. All final compounds were investigated for their in vitro antimicrobial activity. Compounds 6b, 6c, 6d, 6e, and 6h show antimicrobial activity against selected microorganisms compared with the reference drugs.

Experimental

Melting points were determined in open capillaries using an electrical melting point apparatus and are uncorrected. Microwave reactions were carried out in a multi-SYNTH series microwave system (Milestone). The IR spectra were recorded in KBr pellets on a Shimadzu FT-IR-8400s spectrophotometer. The ¹H NMR spectra (400 MHz) and ¹³C NMR spectra (100 MHz) were recorded in CDCl₃ on a Bruker DPX 400 spectrophotometer. The high-resolution electron spray ionization mass spectra (ESI-HR-MS) were recorded on a Micromass Q-Tof (ESI-HR-MS) mass spectrometer.

Synthesis of compounds 6a–i from substrates 5a–i

Conventional method

A mixture of CuSO₄·5H₂O (0.15 mmol), sodium ascorbate (0.15 mmol), benzyl azide (1.5 mmol), and (E)-8-(3-(arylacryloyl)-4-methyl-7-(prop-2-yn-1-yloxy)-2H-chromen-2-one 5a–i (1.5 mmol) in t-BuOH: H₂O (1:1, 5 mL) was stirred at room temperature for 24 h. After completion of the reaction, as monitored by TLC, the mixture was poured onto ice-cold water (20 mL) and extracted with EtOAc (30 mL). The extract was washed twice with saturated solution of NH₄Cl, twice with brine, dried over Na₂SO₄, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (3:1) to afford compound 6a–i.

Microwave irradiation

The mixture indicated above was subjected to MWI at 180 W for 8–10 min. After completion of the reaction, as monitored by TLC, the mixture was worked up and the product 6a–i purified as described above.

Synthesis of compounds 6a–i from the substrate 3

Conventional method

A mixture of 8-acetyl-7-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]-4-methyl-2H-chromen-2-one (3, 1 mmol), an aromatic aldehyde (1 mmol), and few drops of piperidine in ethanol (20 mL) was stirred at room temperature for 24 h. Progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was diluted with cold water and acidified with diluted hydrochloric acid. The resulting precipitate was filtered, dried, and crystallized from ethanol to afford pure chalcone 6a–i.

Microwave irradiation

The mixture described above was placed in a Teflon vial with a screw cap and subjected to MWI at 100 W for 5–6 min. Progress of the reaction was monitored by TLC. Workup and purification of the product 6a–i were conducted as described above.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-cinnamoyl-4-methyl-2H-chromen-2-one (6a)

Pale yellow solid; mp 175–177°C; IR: 3034 (Ar-H), 1728 (C=O of chalcone), 1598 (C=C), 1453 (N=N), 1169 (C-N), 1089 cm^-1 (Ar-O); ¹H NMR: δ 2.41 (s, 3H, CH₃), 5.32 (s, 2H, N-CH₂), 5.38 (s, 2H, O-CH₂), 6.15 (s, 1H, H₃), 6.97 (d, 1H, H_α, J = 16 Hz), 7.13–7.15 (m, 2H, Ar-H), 7.17 (d, 1H, H₆, J = 9 Hz), 7.22–7.47 (m, 10H, H_β, triazole H, Ar-H), 7.62 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 54.2 (N-CH₂), 63.2 (O-CH₂), 109.4, 113.0, 114.6, 122.9, 125.6, 126.5, 127.9, 128.0, 128.03, 128.6, 128.81, 128.82, 128.9, 129.1, 130.9, 134.2, 134.3, 146.4, 151.9, 157.6, 159.8, 191.7 (C=O, chalcone). ESI-HR-MS. Calcd for C₂₉H₂₃N₃O₄Na [M+Na]⁺: m/z 500.1586. Found: m/z 500.1588.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-(4-methoxyphenyl)acryloyl]-4-methyl-2H-chromen-2-one (6b)

Pale yellow solid; mp 205–207°C; IR: 3038 (Ar-H), 1731 (C=O of chalcone), 1600 (C=C), 1459 (N=N), 1173 (C-N), and 1097 cm^-1 (Ar-O). ¹H NMR (400 MHz, CDCl₃) δ (ppm): 2.41 (s, 3H, CH₃), 3.84 (s, 3H, OCH₃), 5.32 (s, 2H, N-CH₂), 5.39 (s, 2H, O-CH₂), 6.15 (s, 1H, H₃), 6.83–7.31 (m, 11H, H_α, Ar-H, H_β), 7.41 (d, 1H, H₆, J = 9 Hz), 7.45 (s, 1H, triazole H), 7.61 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 54.2, 55.4, 63.2, 109.4, 113.0, 114.4, 115.2, 122.8, 123.0, 125.9, 126.3,127.0, 127.9, 128.8, 129.0, 130.2, 130.43, 146.5, 151.3, 156.0, 157.6, 159.9, 161.9, 166.4, 191.6. ESI-HR-MS. Calcd for C₃₀H₂₅N₃O₅Na [M+Na]⁺: m/z 530.1692. Found: m/z 530.1694.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-(3,4-dimethoxyphenyl)acryloyl]-4-methyl-2H-chromen-2-one (6c)

Pale yellow solid; mp 217–219°C; IR: 3040 (Ar-H), 1732 (C=O of chalcone), 1605 (C=C), 1463 (N=N), 1175 (C-N), and 1097 cm^-1 (Ar-O). ¹H NMR: δ 2.42 (s, 3H, -CH₃), 3.81 (s, 3H, OCH₃), 3.98 (s, 3H, OCH₃), 5.32 (s, 2H, N-CH₂), 5.39 (s, 2H, N-CH₂), 6.15 (s, 1H, H₃), 6.82–6.91 (m, 2H, H_α, Ar-H), 7.13–7.39 (m, 9H, H₆, Ar-H, H_β), 7.47 (s, 1H, triazole H), 7.62 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 54.3, 56.4, 57.5, 63.2, 109.3, 113.7, 114.1, 115.6, 122.1, 123.9, 125.2, 126.6, 127.1, 127.7, 128.5, 129.0, 130.2, 130.48, 146.4, 151.3, 151.9, 152.6, 156.2, 157.6, 159.9, 161.9, 166.4, 191.6. ESI-HR-MS. Calcd for C₃₁H₂₇N₃O₆Na [M+Na]⁺: m/z 560.1797. Found: m/z 560.1794.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-4-methyl-8-[3-(3,4,5-trimethoxyphenyl) acryloyl]-2H-chromen-2-one (6d)

Pale yellow solid, mp: 221–223°C; IR: 3040 (Ar-H), 1731 (C=O of chalcone), 1602 (C=C), 1460 (N=N), 1171 (C-N), and 1095 cm^-1 (Ar-O); ¹H NMR: δ 2.42 (s, 3H, CH₃), 3.82 (s, 9H, 3× OCH₃), 5.32 (s, 2H, N-CH₂), 5.40 (s, 2H, O-CH₂), 6.16 (s, 1H, H₃), 6.88 (d, 1H, H_α, J = 16 Hz), 7.17–7.35 (m, 9H, H₆, Ar-H, H_β), 7.47 (s, 1H, triazole H), 7.62 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 54.2, 56.0, 56.2, 61.0, 63.2, 105.6, 109.4, 113.1, 114.5, 123.0, 126.4, 127.4,127.9, 128.0, 128.8, 129.0, 129.1, 129.7, 134.1, 146.5, 151.4, 151.8, 153.4, 153.5, 157.6, 191.6. ESI-HR-MS. Calcd for C₃₂H₂₉N₃O₇Na [M+Na]⁺: 590.1903. Found: m/z 530.1900.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-(4-fluorophenyl)acryloyl]-4-methyl-2H-chromen-2-one (6e)

Pale yellow solid, mp: 185–187°C; IR: 3039 (Ar-H), 1731 (C=O of chalcone), 1600 (C=C), 1460 (N=N), 1173 (C-N), and 1097 cm^-1 (Ar-O). ¹H NMR: δ 2.41 (s, 3H, CH₃), 5.32 (s, 2H, N-CH₂), 5.38 (s, 2H, O-CH₂), 6.17 (s, 1H, H₃), 6.88 (d, 1H, H_α, J = 16 Hz), 6.95–6.98 (m, 2H, Ar-H), 7.04 (d, 1H, H₆, J = 9 Hz), 7.07–7.44 (m, 8H, H_β, Ar-H), 7.47 (s, 1H, triazole H), 7.62 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 54.2, 63.2, 109.4, 113.0, 114.6, 116.0, 116.2, 126.4, 126.5,127.9, 128.0, 128.1, 128.7, 128.8, 129.12, 129.19, 130.5, 130.56, 130.6, 134.2, 145.1, 151.4, 152.0, 157.7, 191.7; ESI-HR-MS. Calcd for C₂₉H₂₂FN₃O₄Na [M+Na]⁺: m/z 518.1492. Found: m/z 518.1490.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-(4-dimethylaminophenyl)acryloyl]-4-methyl-2H-chromen-2-one (6f)

Pale yellow solid; mp 198–200°C IR: 3038 (Ar-H), 1732 (C=O of chalcone), 1600 (C=C), 1459 (N=N), 1172 (C-N), and 1097 cm^-1 (Ar-O); ¹H NMR: δ 2.41 (s, 3H, CH₃), 2.54 (s, 6H, 2× CH₃), 5.31 (s, 2H, N-CH₂), 5.52 (s, 2H, O-CH₂), 6.16 (s, 1H, H₃), 6.63–7.31 (m, 11H, H_α, Ar-H, H_β), 7.40 (d, 1H, H₆, J = 9 Hz), 7.47 (s, 1H, triazole H), 7.74 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 32.4, 54.3, 63.2, 109.3, 111.0, 111.7, 112.9, 114.4, 120.0, 122.1, 122.8, 124.8, 126.4, 128.0, 128.1, 128.9, 129.0, 133.4, 152.0, 154.5, 156.9, 159.7, 162.3, 166.5 199.2. ESI-HR-MS. Calcd for C₃₁H₂₈N₄O₄Na [M+Na]⁺: m/z 543.2008. Found: m/z 543.2010.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-(4-isopropylphenyl)acryloyl]-4-methyl-2H-chromen-2-one (6g)

Pale yellow solid; mp 165–167°C IR: 3035 (Ar-H), 1729 (C=O of chalcone), 1598 (C=C), 1448 (N=N), 1163 (C-N), and 1088 cm^-1 (Ar-O); ¹H NMR: δ 1.2 (s, 6H, (CH₃)₂), 2.41 (s, 3H, CH₃), 2.6 (m, 1H, CH(Me)₂), 5.32 (s, 2H, N-CH₂), 5.38 (s, 2H, O-CH₂), 6.14 (s, 1H, H₃), 6.95 (d, 1H, H_α, J = 16 Hz), 7.12–7.14 (m, 2H, Ar-H), 7.17 (d, 1H, H₆, J = 9 Hz), 7.24–7.44 (m, 8H, H_β, Ar-H), 7.47 (s, 1H, triazole H), 7.62 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 23.8, 32.4, 54.2, 63.2, 109.2, 113.0, 114.4, 122.7, 126.5, 128.1, 128.3, 128.6, 128.80, 128.82, 128.9, 129.1, 130.9, 134.2, 134.3, 143.6, 146.4, 150.4, 151.4 153.6, 159.8, 191.7. ESI-HR-MS. Calcd for C₃₂H₂₉N₃O₄Na [M+Na]⁺: m/z 542.2055. Found: m/z 542.2051.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-[3-(2-chlorophenyl)acryloyl]-4-methyl-2H-chromen-2-one (6h)

Pale yellow solid; mp 183–185°C IR: 3028 (Ar-H), 1731 (C=O of chalcone), 1600 (C=C), 1459 (N=N), 1170 (C-N), and 1097 cm^-1 (Ar-O); ¹H NMR: δ 2.41 (s, 3H, CH₃), 5.32 (s, 2H, N-CH₂), 5.38 (s, 2H, O-CH₂), 6.15 (s, 1H, H₃), 6.88 (d, 1H, H_α, J = 16 Hz), 6.95–6.98 (m, 2H, Ar-H), 7.04 (d, 1H, H₆, J = 9 Hz), 7.07–7.44 (m, 8H, H_β, Ar-H), 7.47 (s, 1H, triazole H), 7.62 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 54.3, 63.2, 109.3, 113.0, 114.5, 126.8, 127.0, 127.2, 128.0, 128.3, 128.8, 129.1, 129.2, 129.5, 130.1, 130.2, 131.5, 134.2, 135.1, 141.6, 142.1, 151.7, 151.9, 157.7, 159.8, 191.6; ESI-HR-MS. Calcd for C₂₉H₂₂ClN₃O₄Na [M+Na]⁺: m/z 534.1196. Found: 534.1192.

(E)-7-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-4-methyl-8-[3-(p-tolyl)acryloyl]-2H-chromen-2-one (6i)

Pale yellow solid; mp 170–172°C; IR: 3038 (Ar-H), 1731 (C=O of chalcone), 1600 (C=C), 1459 (N=N), 1173 (C-N), and 1095 cm^-1 (Ar-O); ¹H NMR: δ 2.41 (s, 3H, CH₃), 2.62 (s, 3H, Ar-CH₃), 5.32 (s, 2H, N-CH₂), 5.38 (s, 2H, O-CH₂), 6.15 (s, 1H, H₃), 6.85 (d, 1H, H_α, J = 16 Hz), 7.05–7.36 (m, 10H, Ar-H, H_β), 7.41 (d, 1H, H₆, J = 9 Hz), 7.45 (s, 1H, triazole H), 7.61 (d, 1H, H₅, J = 9 Hz); ¹³C-NMR: δ 18.7, 29.7, 54.2, 63.2, 109.3, 113.0, 114.4, 122.9, 125.9, 126.3, 126.9, 127.9, 128.0, 128.4, 128.7, 129.0, 130.4, 143.7, 146.4, 151.3, 151.8, 156.0, 157.6, 159.4, 161.9, 191.6. ESI-HR-MS. Calcd for C₃₀H₂₅N₃O₄Na [M+Na]⁺: m/z 514.1742. Found: m/z 514.1725.

Biological activities

All synthesized compounds were screened for their antimicrobial activity against two strains of Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two strains of Gram-negative bacteria (Echerichia coli and Pseudomonas aeruginosa), as well as three strains of fungi (Aspergillus niger, Penicillium italicum, and Fusarium oxysporum). Standard antibiotic drugs amoxicillin for bacteria and mycostatin for fungi were used at a concentration of 50 μg/mL for comparison. The biological activities of these compounds were evaluated by the filter paper disc method [18] for 50 μg/mL solutions in DMF. The inhibition zones of microbial growth surrounding the filter paper disc (5 mm) were measured in millimeters at the end of an incubation period of 3 days at 37°C for E. coli and at 28°C for other bacteria and fungi; DMF alone showed no inhibition zone.

Corresponding author: Ashok Dongamanti, Department of Chemistry, Osmania University, Hyderabad 500 007, India, e-mail: ashokdou@gmail.com

Acknowledgments

The authors are thankful to the head of the Department of Chemistry, Osmania University, Hyderabad, India, for providing laboratory facilities and to the director of CFRD, Osmania University, Hyderabad, India, for providing spectral analysis facilities. One of the authors, B.V.L., is thankful to CSIR, New Delhi, India, for financial support in the form of CSIR-SRF.

References

[1] Gallardo, H.; Conte, G.; Bryk, F.; Lourenço, M. C. S.; Costa, M. S.; Ferreira, V. F. Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agents. J. Braz. Chem. Soc. 2007, 18, 1285–1291.Search in Google Scholar

[2] Jilino, M.; Malcom, S. F. G. Antitumour polycyclic acridines. Part 5.1 Synthesis of 7H-pyrido [4,3,2-kl]acridines with exploitable functionality in the pyridine ring. J. Chem. Soc. 1998, 10, 1677–1684.Search in Google Scholar

[3] Christian, W. T.; Caspar, C.; Morten, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057–3064.Search in Google Scholar

[4] Fan, W. Q.; Katritzky, A. R. 1,2,3-Triazoles. In Comprehensive HeterocyclicChemistry II. Katritzky, A. R.; Rees, C. W.; Scriven, E. F. Eds. Pergamon Press: Oxford, 1996; Vol. 4, pp. 1–126.10.1016/B978-008096518-5.00079-4Search in Google Scholar

[5] Giuliana, B.; Vincenzo, C.; Irene, G.; Oreste, L.; Enrica, M.; Alma, M.; Antonio, N. 1,5-Diarylsubstituted 1,2,3-triazoles as potassium channel activators. VI. Farmaco 2004, 59, 397–404.Search in Google Scholar

[6] Rajasekaran, S.; Rao, G. K.; Pai, S. P. N.; Ranjan, A. Design, synthesis, antibacterial and in vitro antioxidant activity of substituted 2h-benzopyran-2-one derivatives. Int. J. Chem. Tech. Res. 2011, 3, 555–559.Search in Google Scholar

[7] Brahnbhatt, D. I.; Gajera, J. M.; Pandya, V. P.; Patel, M. A. Synthesis of 3-(6-aryl-pyridin-2-yl) and 8-(6-aryl-pyridin-2yl)coumarins. Ind. J. Chem. 2007, 46, 869–871.Search in Google Scholar

[8] Sharma, R.; Arya, V. A. Review on fruits having anti-diabetic potential. J. Chem. Pharm. Res. 2011, 3, 204–212.Search in Google Scholar

[9] RajeshwarRao, V.; Srimanth, K.; VijayaKumar, P. Synthesis of 3-[3-substituted thio]-7H-1,2,4-triazolo[3,4-b] [1,3,4] thiadiazin-6-yl]-2H-1-benzopyran-2-ones and 3-[3-aminoaryl/heterocyclyl]-7H-1,2,4-triazolo [3,4-b] [1,3,4] thiadiazin-6-yl]-2H-1-benzopyran-2-ones. Indian J. Heterocycl. Chem. 2004, 14, 141–144.Search in Google Scholar

[10] Hoeksema, H.; Johnson J. L.; Hinman, J. W. Structural studies on streptonivicin, a new antibiotic. J. Am. Chem. Soc. 1955, 77, 6710–6711.Search in Google Scholar

[11] Pati, H. N.; Holt, H. L. Jr.; Blanc, R. L.; Dickson, J.; Stewart, M.; Brown, T. Synthesis and cytotoxic properties of nitro and aminochalcones. Med. Chem. Res. 2005, 14, 19–25.Search in Google Scholar

[12] Miranda, C. L.; Stevens, J. F.; Ivanov, V.; McCall, M.; Frei, B.; Deinzer, M. L. Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro. J. Agric. Food Chem. 2000, 48, 3876–3884.Search in Google Scholar

[13] Ali, M. A.; Shaharyar, M.; Siddiqui, AA. Synthesis, structural activity relationship and antitubercular activity of novel pyrazoline derivatives. Eur. J. Med. Chem. 2007, 42, 268–275.Search in Google Scholar

[14] Ko, H. H.; Tsao, L. T.; Yu, K. L.; Liu, C. T.; Wang, J. P.; Lin, CN. Structure-activity relationship studies on chalcone derivatives the potent inhibition of chemical mediators release. Bioorg. Med. Chem. 2003, 11, 105–108.Search in Google Scholar

[15] Deshpande, A. M.; Argade, N. P.; Natu, A. A.; Eckman, J. Synthesis and screening of a combinatorial library of naphthalene substituted chalcones: inhibitors of leukotriene B4. Bioorg. Med. Chem. 1999, 7, 1237–1240.Search in Google Scholar

[16] Khatib, S.; Nerya, O.; Musa, R.; Shmnel, M.; Tamir, S.; Vaya, J. Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-disubstituted resorcinol moiety. Bioorg. Med. Chem. 2005, 13, 433–436.Search in Google Scholar

[17] Severi, F.; Benvenuti, S.; Costantino, L.; Vampa, G.; Melegari, M.; Antolini, L. Synthesis and activity of a new series of chalcones as aldose reductase inhibitors. Eur. J. Med. Chem. 1998, 33, 859–862.Search in Google Scholar

[18] Kohno, Y.; Kitamura, S.; Sanoh, S.; Sugihara, K.; Fujimoto, N.; Ohta, S. Metabolism of the α,β-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one by rat liver microsomes and estrogenic activity of metabolites. J. Pharmacol. Exp. Ther. 2005, 33, 1115–1123.Search in Google Scholar

[19] Srinivasan, B.; Johnson, T. E.; Lad, R.; Xing, C. Structure-activity relationship studies of chalcone leading to 3-hydroxy-4,3′,4′,5′-tetramethoxychalcone and its analogues as potent nuclear factor kappaB inhibitors and their anticancer activities. J. Med. Chem. 2009, 52, 7228–7235.Search in Google Scholar

[20] Opdyke, D. L. Monographs on fragrance raw materials. Food Cosmet. Toxicol. 1973, 11, 1011–1081.Search in Google Scholar

[21] El Sayed, H.; El Ashry, E. S. H.; Kassem, A. A. Account of microwave irradiation for accelerating organic reactions of high pressure. Arkivoc 2006, 9, 1–16.Search in Google Scholar

[22] Sarasija, M.; Ashok, D.; Shivaraj. Microwave assisted synthesis of 7-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]-4-methyl-2H-chromen-2-ones and their antibacterial activity. Indian J. Heterocycl. Chem. 2012, 22, 5–8.Search in Google Scholar

[23] Bombardelli, E.; Valenti, P. Preparation of 8-(arylpropenoyl)coumarins as antiproliferative agents. PCT Int. Appl., 15 Mar 2001, WO 2001017984.Search in Google Scholar

Received: 2014-6-26

Accepted: 2014-8-14

Published Online: 2014-10-2

Published in Print: 2014-10-1

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Articles in the same Issue

https://doi.org/10.1515/hc-2014-0102

Keywords for this article

alkyne; azide; chalcone; click chemistry; 1,3-dipolar cycloaddition; triazole

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