• Home
  • Submit Paper
  • Check Paper Status
  • Download Certificate/Paper
  • FAQs
  • Contact Us
Email: ijraset@gmail.com
IJRASET Logo
Journal Statistics & Approval Details
Recent Published Paper
Our Author's Feedback
 •  ISRA Impact Factor 7.894       •  SJIF Impact Factor: 7.538       •  Hard Copy of Certificates to All Authors       •  DOI by Crossref for all Published Papers       •  Soft Copy of Certificates- Within 04 Hours       •  Authors helpline No: +91-8813907089(Whatsapp)       •  No Publication Fee for Paper Submission       •  Hard Copy of Certificates to all Authors       •  UGC Approved Journal: IJRASET- Click here to Check     
  • About Us
    • About Us
    • Aim & Scope
  • Editorial Board
  • Impact Factor
  • Call For Papers
    • Submit Paper Online
    • Current Issue
    • Special Issue
  • For Authors
    • Instructions for Authors
    • Submit Paper
    • Download Certificates
    • Check Paper Status
    • Paper Format
    • Copyright Form
    • Membership
    • Peer Review
  • Past Issue
    • Monthly Issue
    • Special Issue
  • Pay Fee
    • Indian Authors
    • International Authors
  • Topics
ISSN: 2321-9653
Estd : 2013
IJRASET - Logo
  • Home
  • About Us
    • About Us
    • Aim & Scope
  • Editorial Board
  • Impact Factor
  • Call For Papers
    • Submit Paper Online
    • Current Issue
    • Special Issue
  • For Authors
    • Instructions for Authors
    • Submit Paper
    • Download Certificates
    • Check Paper Status
    • Paper Format
    • Copyright Form
    • Membership
    • Peer Review
  • Past Issue
    • Monthly Issue
    • Special Issue
  • Pay Fee
    • Indian Authors
    • International Authors
  • Topics

Ijraset Journal For Research in Applied Science and Engineering Technology

  • Home / Ijraset
  • On This Page
  • Abstract
  • Introduction
  • Conclusion
  • References
  • Copyright

Synthesis and Characterization of Various Pyrazolines From Chalcones

Authors: Pratibha Dwivedi, Dr Alka Pradhan

DOI Link: https://doi.org/10.22214/ijraset.2022.42656

Certificate: View Certificate

Abstract

Some novel series of pyrazoline derivatives were synthesized from Chalcones. Various Pyrazoline derivatives were prepared by reflux reaction of Chalcone with Phenyl Hydrazine Hydrate in ethanolic solution. The structures of the newly synthesized Pyrazoline derivatives have been characterized by spectral data.

Introduction

I. INTRODUCTION

 Because bacterial resistance to antibacterial drugs is rapidly developing, it is critical to develop new scaffolds for the design and synthesis of new antibacterial agents to help in the fight against harmful germs. Chalcones are a class of natural and synthetic compounds that have a wide variety of pharmacological actions, including antibacterial1, antitumour2, anticancer3, antitubercular4, antiinflammatory5, antioxidant6, antimalarial7, antileishmanial8, and other properties. The biological activity of chalcones is determined to be due to the presence of a reactive, -unsaturated keto group. In this study, chalcones were made by condensing different ketones with aromatic aldehyde via claisen Schmidt condensation. According to available evidence, N-containing heterocyclic compounds derived from chalcones have a wide range of activities9-17, including possible cytotoxic, antibacterial, antiviral, anti-inflammatory, anaesthetic, and mydriatic properties.

II. MATERIALS AND METHOD

All of the reagents and solvents used were of the highest quality. Which were used without being purified further. Melting points were measured using standardized melting point equipment. UV-Visible absorption spectra in DMSO were recorded using a SHIMADZU UV-1800 spectrometer with more than a concentration range of 104 M. In KBr pellets, IR spectra were obtained on an FT-IR-Alpha Bruker IR spectrometer from 4000 cm1 to 400 cm1. The 1H and 13C NMR spectra in DMSO-d6 were acquired at 500 MHz using an AV500 Resolution Multinuclear FT-NMR Spectrometer with tetramethylsilane as the internal standard. In sterile distilled water, a working stock of 100 mg/ml concentration of the given drug samples identified as "pyrazoline derivatives" was prepared.

III. SYNTHESIS

(Z)-2-benzylidene-N1-(((2-hydroxy-3-nitrophenyl)(4-methoxyphenyl)methyl)carbamothioyl)-N3-(((2-hydroxyphenyl)(4-methoxyphenyl)methyl)carbamothioyl) malonamide (0.01 mole)  In 100% ethanolic medium, malonamide  and hydrazine hydrate (0.01 mole) were refluxed for 1 hour. When the mixture was filtered under suction and recrystallized from ethanol, it was cooled and poured on crushed ice, and recrystallized from ethanol.

IV. EXPERIMENTAL DATA

Comp. Code

Chemical formula

Molecular weight

Elemental analysis

Appearance

Melting point

Yield

V(1)

C44H41N7O6S

795.28

C (66.40%) H (5.19%)

N (12.32%)

O (12.06%)  S (4.03%)

 

Brown

1850C

 

V(2)

C42H41N6O6SCl

 

792.25

 

C (63.59%) H (5.21%)

N (10.59%) O (12.10%)  S (4.04%) Cl (4.47)

Brown

1820C

50%

V(3)

C41H39N7O8S

789.26

C (62.35%) H (4.98%)

N (12.41%) O (16.20%)  S (4.06%)

Yellow

1800C

53%

V(4)

C41H40N6O7S

 

760.27

C (64.72%) H (5.30%)

N (11.05%) O (14.72%)  S (4.21%)

Brown

1650C

55%

V(5)

C42H42N6O6S

 

758.29

C (66.47%) H (5.58%)

N (11.07%) O (12.65%)  S (4.22%)

White

1620C

47%

V(1): N-(((5-amino-2-hydroxyphenyl)(4-methoxyphenyl)methyl)carbamoyl)-3-(3-((1-hydroxynaphthalen-2-yl)(4-methoxyphenyl)methyl)thioureido)-5-phenyl-4,5-dihydro-1H-pyrazole-4-carboxamide:

IR (KBr) cm-1: 3705(Ar-OH stretching), 1413(C=N stretching) 1650 (C=O) 3315 (N-H stretching for 20 amines) 1491 (C=S), 1078 (C-N stretching) 1363 (OH bending). 755 (N-H wagging)

1HNMR (CDCl3) δ: 13.01(s,1H NH), 8.12 (d,1H,NH), 9.92 (d,1H,NH Pyrazoline ring) 4.12 (dd, 1H, CH pyrazoline ring)  2.9 (d,1H CH pyrazoline ring) 9.65 (s,1H,Ar-OH), 5.26(s,1H,CH), 7.26, 7.35, 6.99, 6.86 (m, 4H, Ar-H)   8.05, 7.43, 7.22,(m, 3H, Ar-H), 7.32, 7.36. 7.26, 7.33, 7.35(m 5H Ar-H) 3.81(s,3H CH3)

13CNMR (CDCl3) δ: 52.2 (1C, CH, of pyrazoline ring) 46.23 (1C, CH of Pyrazoline ring) 175.4 (1C, C=O) 184 (1C C=S) 61 (1C, CH) 57.1 (1C OCH3) 155, 135,136, 120,127 (6C-C6H5) 128 (6C-C6H5)

V(2): N-(((3-chloro-4-hydroxyphenyl)(4-methoxyphenyl)methyl)carbamoyl)-3-(3-((4-hydroxy-3-methylphenyl)(4-methoxyphenyl)methyl)thioureido)-5-phenyl-4,5-dihydro-1H-pyrazole-4-carboxamide:

IR (KBr) cm-1: 3698(Ar-OH stretching), 1415(C=N stretching) 1654 (C=O) 3215 (N-H stretching for 20 amines) 1491 (C=S), 1078 (C-N stretching) 1363 (OH bending). 755 (N-H wagging)

1HNMR (CDCl3) δ: 13.07(s,1H NH), 8.1 (d,1H,NH), 9.92 (d,1H,NH Pyrazoline ring) 4.1 (dd, 1H, CH pyrazoline ring)  2.81 (d,1H CH pyrazoline ring) 9.63 (s,1H,Ar-OH), 5.16(s,1H,CH), 7.21, 7.32, 6.89, 6.85 (m, 4H, Ar-H)   8.05, 7.43, 7.22,(m, 3H, Ar-H), 7.32, 7.35. 7.25, 7.32, 7.35(m 5H Ar-H) 3.81(s, 3H CH3)

13CNMR (CDCl3) δ: 52.11 (1C, CH, of pyrazoline ring) 47.23 (1C, CH of Pyrazoline ring) 175.4 (1C, C=O) 184 (1C C=S) 61 (1C, CH) 57.1 (1C OCH3) 155, 135,136, 120,127 (6C-C6H5) 128 (6C-C6H5)

V(3): 3-(3-((4-hydroxy-3-methylphenyl)(4-methoxyphenyl)methyl)thioureido)-N-(((2-hydroxy-5-nitrophenyl)(4-methoxyphenyl)methyl)carbamoyl)-5-phenyl-4,5-dihydro-1H-pyrazole-4-carboxamide:

IR (KBr) cm-1: 3705(Ar-OH stretching), 1413(C=N stretching) 1650 (C=O) 3315 (N-H stretching for 20 amines) 1491 (C=S), 1078 (C-N stretching) 1363 (OH bending). 755 (N-H wagging)

1HNMR (CDCl3) δ: 13.07(s,1H NH), 8.2 (d,1H,NH), 9.92 (d,1H,NH Pyrazoline ring) 4.15 (dd, 1H, CH pyrazoline ring)  2.7 (d,1H CH pyrazoline ring) 9.65 (s,1H,Ar-OH), 5.14(s,1H,CH), 7.21, 7.32, 6.89, 6.85 (m, 4H, Ar-H)   8.05, 7.43, 7.22,(m, 3H, Ar-H), 7.32, 7.35. 7.25, 7.32, 7.35(m 5H Ar-H) 3.81(s, 3H CH3)

13CNMR (CDCl3) δ: 52.11 (1C, CH, of pyrazoline ring) 47.23 (1C, CH of Pyrazoline ring) 175.4 (1C, C=O) 184 (1C C=S) 61 (1C, CH) 57.1 (1C OCH3) 155, 135,136, 121,126 (6C-C6H5) 128.2 (6C-C6H5)

V(4): N-(((2,4-dihydroxyphenyl)(4-methoxyphenyl)methyl)carbamoyl)-3-(3-((4-hydroxy-3-methylphenyl)(4-methoxyphenyl)methyl)thioureido)-5-phenyl-4,5-dihydro-1H-pyrazole-4-carboxamide:

 IR (KBr) cm-1: 3695(Ar-OH stretching), 1413(C=N stretching) 1650 (C=O) 3315 (N-H stretching for 20 amines) 1491 (C=S), 1078 (C-N stretching) 1363 (OH bending). 755 (N-H wagging)

1HNMR (CDCl3) δ: 13.27(s,1H NH), 8.1 (d,1H,NH), 9.91 (d,1H,NH Pyrazoline ring) 4.10 (dd, 1H, CH pyrazoline ring)  2.8 (d,1H CH pyrazoline ring) 9.63 (s,1H,Ar-OH), 5.16 (s,1H,CH), 7.31, 7.33, 6.89, 6.84 (m, 4H, Ar-H)   8.05, 7.43, 7.24,(m, 3H, Ar-H), 7.32, 7.34. 7.26, 7.32,7.35(m 5H Ar-H) 3.81(s,3H CH3)

13CNMR (CDCl3) δ: 52.11 (1C, CH, of pyrazoline ring) 47.23 (1C, CH of Pyrazoline ring) 175.4 (1C, C=O) 182.1 (1C C=S) 61 (1C, CH) 57.01 (1C OCH3) 155, 134,136, 120,127.5 (6C-C6H5) 128 (6C-C6H5)

V(5): 3-(3-((4-hydroxy-3-methylphenyl)(4-methoxyphenyl)methyl)thioureido)-N-(((2-hydroxy-5-mehtylphenyl)(4-methoxyphenyl)methyl)carbamoyl)-5-phenyl-4,5-dihydro-1H-pyrazole-4-carboxamide:

IR (KBr) cm-1: 3707(Ar-OH stretching), 1415(C=N stretching) 1651 (C=O) 3310 (N-H stretching for 20 amines) 1491 (C=S), 1077 (C-N stretching) 1362 (OH bending). 756 (N-H wagging)

1HNMR (CDCl3) δ: 13.17(s,1H NH), 8.1 (d,1H,NH), 9.82 (d,1H,NH Pyrazoline ring) 4.2 (dd, 1H, CH pyrazoline ring)  2.81 (d,1H CH pyrazoline ring) 9.63 (s,1H,Ar-OH), 5.16(s,1H,CH), 7.21, 7.02, 6.89, 6.65 (m, 4H, Ar-H)   8.15, 7.43, 7.22,(m, 3H, Ar-H), 7.43, 7.31. 7.25, 7.32, 7.31(m 5H Ar-H) 3.81(s,3H CH3)

13CNMR (CDCl3) δ: 50.43 (1C, CH, of pyrazoline ring) 46.23 (1C, CH of Pyrazoline ring) 174.4 (1C, C=O) 186.5 (1C C=S) 61.1 (1C, CH) 55.1 (1C OCH3) 153, 135,137, 121,128 (6C-C6H5) 128 (6C-C6H5)

Conclusion

In this study, we have successfully synthesized new pyrazolines derivatives compounds. The proper analysis of the synthesis of new pyrazolines derivatives has been systematically evaluated by FT-IR, NMR, Mass spectrometry.

References

[1] Hogale M.B., Dhore N.P., Shelar A.R. and Pawar P.K., Orient J. Chem., 1986, 2, 55. [2] Yamakawa T., Kagechika H., Kawachi E., Hashimoto Y. and Shedo K., J. Med. Chem., 1990, 33, 1430. [3] Ahluwalia V.K., Nayal L., Kalia N., Bala S. and Tahim, A.K., Indian J. Chem., 1987, 26B, 384. [4] Bhatt A.K., Bhamaria R.P., Patel M.R., Bellare R.A. and Deliwala, Indian J. Chem., 1972, 10, 694. [5] Mukherjee S., Kumar V., Prasad A.K., Raj H.G., Brakhe M.E., Olsen C.E., Jain S.C Bio-org. Med.Chem., 2001, 9, 337. [6] Indyah S.A., Timmerman H., Samhoedi M., Sastronami., Sugiyanto and Goot H.V. Eur. J. Med. Chem., 2000, 35, 449-457. [7] Chen M., Christensen S., Zhai L., Rasmussen M.H., Theander T.G., Frokjaer S., Steffensen B., Davidson J. and Kharazmi, A. J.Infect. Dis., 1997, 176(5), 1327-1333. [8] Nielsen S.F., Christensen S.B., Cruciani G. Kharazmi A., and Liljefors, T., Antileishmanial chalcones, J. Med. Chem., 1998, 41, 4819-4832. [9] Vibhute Y.B. and Basser M.A., Ind.J. of Chem., 2003, 42B, 202-205. [10] Bhat B.A., Dhar K.L., Saxena A.K. and Shanmugavel M., Bio org. & Med. Chem., 2005, 15(3), 177-3180. [11] Edwards M.L., Stemerick D.M. and Sunkara P.S., J. of Med. Chem., 1990, 33, 1948-54. [12] Kalirajan R., Palanivelu M., Rajamanickam V., Vinothapooshan G. and Anandarajagopal K.,Int. J. of Chem. Sci., 2007, 5(1), 73-80. [13] Udupi R. H., Bhat R., and Kumar K., Indian J. of Het.Chem., 1998, 8, 143-146. [14] Pande A.and Saxena V.K., Ind.J.of Chem., 1987, 26B ,390-392. [15] Gupta U., Sareen V., Khatri V. and Chugh, S., Indian J. of Het.Chem., 2005, 14, 265-266. [16] Pandey V.K., Gupta V.D. and Tiwari D.N., Indian J. of Het. Chem., 2004, 13, 399-400. [17] Mishra R.M. and Wahab, A., Indian J. of Het. Chem., 2003, 13, 29-32. [18] Pharmacopoeia of India, 1996, II, A-100, A-108.

Copyright

Copyright © 2022 Pratibha Dwivedi, Dr Alka Pradhan. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

ijraset42656Pratibha

Download Paper

Authors : pratibha dwivedi

Paper Id : IJRASET42656

Publish Date : 2022-05-13

ISSN : 2321-9653

Publisher Name : IJRASET

DOI Link : Click Here

About Us

International Journal for Research in Applied Science and Engineering Technology (IJRASET) is an international peer reviewed, online journal published for the enhancement of research in various disciplines of Applied Science & Engineering Technologies.

Quick links
  • Privacy Policy
  • Refund & Cancellation Policy
  • Shipping Policy
  • Terms & Conditions
Quick links
  • Home
  • About us
  • Editorial Board
  • Impact Factor
  • Submit Paper
  • Current Issue
  • Special Issue
  • Pay Fee
  • Topics
Journals for publication of research paper | Research paper publishers | Paper publication sites | Best journal to publish research paper | Research paper publication sites | Journals for paper publication | Best international journal for paper publication | Best journals to publish papers in India | Journal paper publishing sites | International journal to publish research paper | Online paper publishing journal

© 2022, International Journal for Research in Applied Science and Engineering Technology All rights reserved. | Designed by EVG Software Solutions