Synthesis of novel 2-amino-4-(5′-substituted 2′-phenyl-1H- indol-3′-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents

DOI: 10.1016/j.bmcl.2013.02.036

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Bioorganic and Medicinal Chemistry Letters p. 1978 - 1984 (2013)

Update date:2022-08-04

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Authors:

Saundane, Anand R.

Vijaykumar, Katkar

Vaijinath, A. Verma

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Article abstract of DOI:10.1016/j.bmcl.2013.02.036

As a part of systematic investigation of synthesis and biological activities of indole analogues linked to various heterocyclic systems, we have synthesized new compounds viz., 2-amino-4-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-6-aryl-4H-pyran-3-carbonitriles (2a-i), 4,5-diamino-6-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-8- aryl-2-oxo-2,6-dihydrodipyrano [2,3-b:3,2-e]pyridine-3-carbonitriles (3a-i), 4-amino-5-(5′-substituted 2′-phenyl-1H-indol-3-yl)-7-aryl-1H- pyrano[2,3-d]pyrimidin-2(5H)-ones (4a-i), 4-amino-5-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H) -thiones (5a-i), 4-(5′-subtituted 2′-phenyl-1H-indol-3′-yl)-6- aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines (6a-i) and 5-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-7-aryl-3H-pyrano[2,3-d]pyrimidin-4(5H)- ones (7a-i). Antibacterial activity results revealed that, compound 6a showed promising activity versus Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 6d exhibited good activity against S. aureus, K. pneumoniae and Pseudomonas aeruginosa. Antifungal activity results indicated that, compound 4d exhibited maximum zone of inhibition against Aspergillus oryzae and Aspergillus flavus. In case of antioxidant activity, compound 4a showed promising radical scavenging activity, ferric ions (Fe³⁺) reducing antioxidant power (FRAP) and metal chelating activity.

Full text of DOI:10.1016/j.bmcl.2013.02.036

Bioorganic & Medicinal Chemistry Letters 23 (2013) 1978–1984

Contents lists available at SciVerse ScienceDirect

Bioorganic & Medicinal Chemistry Letters

journal homepage: w ww.elsevier.com/locate/bmcl

Synthesis of novel 2-amino-4-(5⁰-substituted 2⁰-phenyl-

1H-indol-3⁰-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives

as antimicrobial and antioxidant agents

Anand R. Saundane ^a,, Katkar Vijaykumar , A. Verma Vaijinath

⇑

^aDepartment of Post-Graduate Studies and Research in Chemistry, Gulbarga University, Gulbarga 585 106, Karnataka, India

^bShri Prabhu Arts, Science and J. M. Bohra Commerce College, Shorapur 585 224, Karnataka, India

a r t i c l e i n f o

a b s t r a c t

Article history:

As a part of systematic investigation of synthesis and biological activities of indole analogues linked to

various heterocyclic systems, we have synthesized new compounds viz., 2-amino-4-(5⁰-substituted

2⁰-phenyl-1H-indol-3⁰-yl)-6-aryl-4H-pyran-3-carbonitriles (2a–i), 4,5-diamino-6-(5⁰-substituted 2⁰-phe-

nyl-1H-indol-3⁰-yl)-8-aryl-2-oxo-2,6-dihydrodipyrano [2,3-b:3,2-e]pyridine-3-carbonitriles (3a–i), 4-

amino-5-(5⁰-substituted 2⁰-phenyl-1H-indol-3-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-ones (4a–i),

4-amino-5-(5⁰-substituted 2⁰-phenyl-1H-indol-3⁰-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-thiones

(5a-i), 4-(5⁰-subtituted 2⁰-phenyl-1H-indol-3⁰-yl)-6-aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines (6a–

i) and 5-(5⁰-substituted 2⁰-phenyl-1H-indol-3⁰-yl)-7-aryl-3H-pyrano[2,3-d]pyrimidin-4(5H)-ones (7a–i).

Antibacterial activity results revealed that, compound 6a showed promising activity versusEscherichia coli,

Staphylococcus aureus and Klebsiella pneumoniae. Compound 6d exhibited good activity against S. aureus, K.

pneumoniae and P. aeruginosa. Antifungal activity results indicated that, compound 4d exhibited maximum

zone of inhibition againstAspergillus oryzae andAspergillus ﬂavus. In case of antioxidant activity, compound

4a showed promising radical scavenging activity, ferric ions (Fe⁺³) reducing antioxidant power (FRAP) and

metal chelating activity.

Received 23 July 2012

Revised 1 February 2013

Accepted 7 February 2013

Available online 16 February 2013

Keywords:

Indole

Pyran

Pyranopyrimidine

Pyranopyrazole

Antimicrobial

Antioxidant

The emergence and spread of antimicrobial resistance has

become one of the most serious public health concern across the

world. Antimicrobial resistance refers to micro-organism that has

developed the ability to inactivate, exclude or block the inhibitory

or lethal mechanism of the antimicrobial agents.¹Electron-rich

nitrogen heterocycles play an important role in diverse medicinal

chemistry.²Indole derivatives substituted at C-3 position by

2-amionopyrimidine ring were successfully evaluated for their

ability to inhibit various protein kinases³also displayed antitumor

activity.⁴Numerous methods for the synthesis of indole derivatives

and also their various reactions offer enormous scope in the ﬁeld of

medicinal chemistry such as antitumor,^5–8anti-inﬂammatory,^9–11

antioxidant,¹²etc. agents. In addition, 4H-pyran derivatives consti-

tute a useful class of heterocyclic compounds which are widely dis-

tributed in nature.^13,14These compounds display wide range of

biological activities, acting as fungicides, herbicides and a variety

of pharmacological properties, which could be useful in the treat-

ment of asthma and allergies.¹⁵

In our previous communication,¹⁶we have reported the synthe-

sis, antioxidant and antimicrobial activities of indole analogues in

which 3-cyano-2-aminopyridine (1), pyranonapthyridines (2),

R¹

NH₂NH₂

NH₂

R²

R¹

NH₂

R²

X = O or S

⇑

Corresponding author. Tel.: +91 9480272325.

E-mail addresses: arsaundane@rediff.com (A.R. Saundane), tkvijaykumar@

Figure 1. Motivation for synthesis of antibacterial and antioxidant active

rediffmail.com (K. Vijaykumar), vverma_chem@rediffmail.com (A.V. Vaijinath).

compounds.

http://dx.doi.org/10.1016/j.bmcl.2013.02.036

A. R. Saundane et al. / Bioorg. Med. Chem. Lett. 23 (2013) 1978–1984

1979

pyridopyrimidine (3) and pyrazolopyridine (4) (Fig. 1) linked to 3-

position of indole. Some of these compounds exhibited good antimi-

crobial and antioxidant activities. Prompted by these results and in

continuation of our research work in the synthesis of biologically

important heterocyclic compounds,¹⁷we herein report the synthe-

sis of title compounds in which pyridine system is replaced by the

dihydropyran nucleus in the above heterocycles (1–4) to evaluate

the impact of these compounds on their antimicrobial and antioxi-

dant activities.

R¹

R²

NH₂

1a-i

2a-i

R²

R¹: Cl CH₃

R²: Cl Cl Cl CH₃CH₃CH₃

Cl CH₃

3-(5⁰-Substituted 2⁰-phenyl-1H-indol-3⁰-yl)-1-arylprop-2-en-1-

ones 1a–i were synthesized by a base catalyzed Claisen–Schmidt

condensation of 4-substituted acetophenones with 5-substituted

Scheme 1. Reagents and conditions: (a) CH₂(CN)₂/COONa, acetic acid, reﬂux 3 h.

R¹

NH₂

4a-i

R²

3a-i

2a-i

R¹

NH₂

R¹

R²

5a-i

6a-i

R²

7a-i

R¹: Cl CH₃

Cl CH₃

R²: Cl Cl Cl CH₃CH₃CH₃

Scheme 2. Reagents and conditions: (a) CNCH₂COOEt, Et₃N, ethanol, reﬂux, 2 h; (b) NH₂CONH₂, ethanol, reﬂux, 5 h; (c) NH₂CSNH₂, ethanol, reﬂux, 5 h; (d) N₂H₄H₂O, ethanol,

reﬂux, 3 h; (e) HCOOH, reﬂux, 6 h.

Table 1

In vitro antibacterial activities of compounds 2–7

Compd no.

Concd (

g/ml) (zone of inhibition in mm)

E. coli

S. aureus

K. pneumoniae

P. aeruginosa

1000

750

500

1000

750

500

1000

750

500

1000

750

500

(continued on next page)

1980

A. R. Saundane et al. / Bioorg. Med. Chem. Lett. 23 (2013) 1978–1984

Table 1 (continued)

Compd no.

Concd (lg/ml) (zone of inhibition in mm)

E. coli

S. aureus

K. pneumoniae

P. aeruginosa

1000

750

500

1000

750

500

1000

750

500

1000

750

500

Std.

Std = Streptomycin (Standard).

Table 2

In vitro antifungal activity of compounds 2–7

Compd no.

Concd (lg/ml) (zone of inhibition in mm)

A. nizer

A. oryzae

A. terrus

A. ﬂavus

1000

750

500

1000

750

500

1000

750

500

1000

750

500

—

A. R. Saundane et al. / Bioorg. Med. Chem. Lett. 23 (2013) 1978–1984

1981

Table 2 (continued)

Compd no.

Concd (

g/ml) (zone of inhibition in mm)

A. nizer

A. oryzae

A. terrus

A. ﬂavus

1000

750

500

1000

750

500

1000

750

500

1000

750

500

—

Std.

Std = Fluconazole (Standard).

Concentration (µg/mL)

Concentration (µg/mL

Figure 4. RSA of compounds 4a–i at different concentrations (25, 50, 75 and

100 g/ml).

Figure 2. RSA of compounds 2a–i at different concentrations (25, 50, 75 and

100 g/ml).

Concentration (µg/mL)

Figure 3. RSA of compounds 3a–i at different concentrations (25, 50, 75 and Figure 5. RSA of compounds 5a–i at different concentrations (25, 50, 75 and

100 g/ml). 100 g/ml).

1982

A. R. Saundane et al. / Bioorg. Med. Chem. Lett. 23 (2013) 1978–1984

Concentration (µg/mL)

Figure 9. FRAP of compounds 3a–i at different concentrations (25, 50, 75 and

100 g/ml).

Figure 6. RSA of compounds 6a–i at different concentrations (25, 50, 75 and

100 g/ml).

Figure 10. FRAP of compounds 4a–i at different concentrations (25, 50, 75 and

100 g/ml).

Concentration (µg/mL)

Figure 7. RSA of compounds 7a–i at different concentrations (25, 50, 75 and

100 g/ml).

Figure 11. FRAP of compounds 5a–i at different concentrations (25, 50, 75 and

100 g/ml).

Concentration (µg/mL)

(5⁰-substituted 2⁰-phenyl-1H-indol-3⁰-yl)-7-aryl-1H-pyrano[2,3-

d]pyrimidin-2(5H)-thiones 5a–i, 4-(5⁰-subtituted 2⁰-phenyl-1H-in-

dol-3⁰-yl)-6-aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines 6a–i

and 5-(5⁰-substituted 2⁰-phenyl-1H-indol-3⁰-yl)-7-aryl-3H-pyr-

ano[2,3-d]pyrimidin-4(5H)-ones 7a–i, respectively in good yield

(Scheme 2). The synthesized compounds were characterized by

elemental and spectral analyses (please see Supplementary data).

All the synthesized compounds (2–7) were evaluated for their

antibacterial activity against Escherichia coli (MTCC-723), Staphylo-

coccus aureus (ATCC-29513), Klebsiella pneumoniae (NCTC-13368)

and Pseudomonas aeruginosa (MTCC-1688) and antifungal activity

against Aspergillus niger (MTCC-281), Aspergillus oryzae (MTCC-

3567^T), Aspergillus terrus (MTCC-1782) and Aspergillus ﬂavus

(MTCC-1973) by cup-plate method¹⁹(Tables 1 and 2). The zone

of inhibition (in mm) was compared with standards streptomycin

and ﬂuconazole for antibacterial and antifungal activities, respec-

Figure 8. FRAP of compounds 2a–i at different concentrations (25, 50, 75 and

100 g/ml).

2-phenyl-1H-indol-3-carboxaldehydes.¹⁸Compounds 1a–i were

subjected to cyclocondensation with malononitrile in presence of

sodium acetate to afford 2-amino-4-(5⁰-substituted 2⁰-phenyl-1H-

indol-3⁰-yl)-6-aryl-4H-pyran-3-carbonitriles 2a–i in high yield

(Scheme 1).

The compounds 2a–i when subjected to heterocyclization with

economically viable and easily available reagents such as, ethyl

cyanoacetate, urea, thiourea, hydrazine hydrate and formic acid

afforded 4,5-diamino-6-(5⁰-substituted 2⁰-phenyl-1H-indol-3⁰-yl)-

8-aryl-2-oxo-2,6-dihydrodipyrano[2,3-b:3,2-e]pyridine-3-carbo-

nitriles 3a–i, 4-amino-5-(5⁰-substituted 2⁰-phenyl-1H-indol-3⁰-yl)-

7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-ones 4a–i, 4-amino-5-

A. R. Saundane et al. / Bioorg. Med. Chem. Lett. 23 (2013) 1978–1984

1983

Concentration (µg/mL)

Figure 12. FRAP of compounds 6a–i at different concentrations (25, 50, 75 and

100 g/ml).

Figure 16. Metal chelating activity of compounds 4a–i at different concentrations

(25, 50, 75 and 100

lg/ml.)

Concentration (µg/mL)

Figure 17. Metal chelating activity of compounds 5a–i at different concentrations

(25, 50, 75 and 100 g/ml).

Figure 13. FRAP of compounds 7a–i at different concentrations (25, 50, 75 and

100 g/ml).

Concentration (µg/mL)

Figure 18. Metal chelating activity of compounds 6a–i at different concentrations

(25, 50, 75 and 100

lg/ml).

Figure 14. Metal chelating activity of compounds 2a–i at different concentrations

(25, 50, 75 and 100

lg/ml).

Concentration (µg/mL)

Figure 19. Metal chelating activity of compounds 7a–i at different concentrations

(25, 50, 75 and 100 g/ml).

Concentration (µg/mL)

Figure 15. Metal chelating activity of compounds 3a–i at different concentrations

(25, 50, 75 and 100 g/ml).

1984

A. R. Saundane et al. / Bioorg. Med. Chem. Lett. 23 (2013) 1978–1984

tively. The in vitro antioxidant activity was evaluated by three dif-

ferent methods viz., radical scavenging activity²⁰(RSA), ferric ions

(Fe⁺³) reducing antioxidant power²¹(FRAP) and metal chelating

activity²²of ferrous ions. Most of the compounds exhibited signif-

icant to moderate activities.

may be due to the non-aromatic character of pyran ring. Thus,

the preliminary results showed that the pyridine ring plays an

important role to enhance antimicrobial and antioxidant activities.

Acknowledgements

Antibacterial screening revealed that, compound 6a having

chloro substitution at C-5 position of indole and C-4 position aryl

ring along with pyranopyrazole system enhanced the activity

against E. coli, S. aureus and K. pneumoniae at all concentrations.

Compounds 2a, 3a–c, 4c, 4e and 6e exhibited maximum zone of

inhibition against E. coli at all concentrations. The compounds 2a,

2e, 3b, 3g, 4a, 4c, 5a and 6d showed good zone of inhibition against

S. aureus at all concentrations whereas, the compounds 2i, 3a, 3c,

6b, 6d and 7a showed maximum zone of inhibition against K. pneu-

moniae at all concentrations. Compounds 2g, 4c, 4i, 6d, 6g and 6i

showed good zone of inhibition against P. aeruginosa at all

concentrations.

The authors are thankful to the Chairman, Department of Chem-

istry, Gulbarga University, Gulbarga, for providing laboratory facili-

ties, Chairman, Department of Microbiology, Gulbarga University,

Gulbarga for providing facilities to carry out antimicrobial activity

and also thankful to Director, Indian Institute of Technology, Ma-

dras, Chennai for providing spectral data. One of us (V.K.) is thankful

to University Grants Commission, New Delhi, India for providing

ﬁnancial assistance through Research Fellowship in Science Merito-

rious Students (RFSMS).

Supplementary data

Antifungal activity assay revealed that, the compound 4d exhib-

ited maximum zone of inhibition against A. oryzae and A. ﬂavus.

This enhanced activity of 4d may be due to presence of chloro sub-

stitution at C-5 position of indole and methyl substitution at C-4

position of aryl ring. Replacement of chloro substitution (com-

pound 4d) at C-4 position of aryl ring by methyl group (compound

7d) and shifting of oxo group from 2- to 4-position, that is, in place

of amino group showed increase in antifungal activity against A.

oryzae and A. ﬂavus. Compounds 4a, 5a and 5i showed potent activ-

ity against Aspergillus niger, whereas compounds 2e, 3c, 3g, 4g, 6c,

6g and 7g exhibited high activity against A. oryzae. Compounds 2b,

2c and 3a showed potent activity against Aspergillus terrus,

whereas, compounds 2a, 3e and 4c showed good activity against

A. ﬂavus at all concentrations.

Supplementary data associated with this article can be found, in

the online version, at http://dx.doi.org/10.1016/j.bmcl.2013.02.

036.

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indole and C-4 position of aryl ring (compound 4a) was found to

enhance the RSA (75.54% at 100

good RSA at 50 g/ml concentration. Compounds 3d, 5a and 7a

showed promising activity at 75 g/ml concentration. Compounds

lg/ml). Compound 7a exhibited

2a, 2i, 4f, 6b and 6e exhibited good RSA at 100 lg/ml

concentration.

The FRAP results (Figs. 8–13, please see Supplementary data) re-

vealed that, compound 7d showed higher activity by introduction

of chloro substitution at C-5 position of indole and methyl group at

C-4 position of aryl ring was found to enhance the FRAP, com-

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pounds 5b and 7d exhibited promising activity at 25 and 75

ml concentrations and compounds 3a, 4a and 6c showed good

activity at 75 g/ml concentration, whereas the compounds 2f,

6a, 6d and 7h exhibited good activity at 100 g/ml concentrations.

lg/

Ferrous ions (Fe²⁺) metal chelating activity capacity (Figs. 14–

19, please see Supplementary data) of the title compounds indi-

cated that, introduction of chloro substitution at C-5 position of

indole and C-4 position of aryl ring (compound 3a) exhibited high-

er metal chelating activity (79.71% at 100 lg/ml). Compounds 2d,

3h, 4a, 4i, 5c, 5i, 6a, 6f, 6h, 7a, 7d, 7f and 7g exhibited good metal

chelating activity at all concentrations, whereas other compounds

exhibited either moderate or poor chelating activity.

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Article Doi

Synthesis of novel 2-amino-4-(5′-substituted 2′-phenyl-1H- indol-3′-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents

DOI: 10.1016/j.bmcl.2013.02.036

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Full text of DOI:10.1016/j.bmcl.2013.02.036

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