GET THE APP

Synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane derivatives as Antimicrobial agents

Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

ISSN: 0975-413X
All submissions of the EM system will be redirected to Online Manuscript Submission System. Authors are requested to submit articles directly to Online Manuscript Submission Systemof respective journal.

Research Article - Der Pharma Chemica ( 2022) Volume 14, Issue 12

Synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane derivatives as Antimicrobial agents

Awinash S. Chavan1* and Seema P. Rathod2
 
1Department of chemistry, Raosaheb Patil Danve College of Pharmacy Badnapur, Dr. Babasaheb Ambedkar Technological University Lonere, Raigad, India
2School of Pharmacy Nanded, Swami Ramanand Teerth Marathwada University Nanded, India
 
*Corresponding Author:
Awinash S. Chavan, Department of chemistry, Raosaheb Patil Danve College of Pharmacy Badnapur, Dr. Babasaheb Ambedkar Technological University Lonere, Raigad, India, Email: avichavan4741@gmail.com

Received: 05-Dec-2022, Manuscript No. dpc-22-82303; Editor assigned: 07-Dec-2022, Pre QC No. dpc-22-82303; Reviewed: 21-Dec-2022, QC No. dpc-22-82303; Revised: 23-Dec-2022, Manuscript No. dpc-22-82303; Published: 30-Dec-2022, DOI: 10.4172/0975-413X.14.12.25-28

Abstract

Epoxides are the natural phytoconstituents with several biological significance such as Anti-inflammatory, Antioxidant, Anticancer and Antimicrobial activity. The Series 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane derivatives was designed and synthesized from 1-(5-chloro-2-hydroxyphenyl)-3-(2-chlorophenyl)-prop-2-en-1-one.

Current research work screened forIv-vitroanti-bacterial activity against Escherichia coli, Staphylococcus aureus (Pathogens obtained from animal), Xanthomonas citri and Xanthomonas malvacearum (Pathogens obtained from plant). The compound SAC-3 and SAC-6 shows good antibacterial activity while other shows moderate to good anti-microbial activity.

Keywords

Epoxide; Chalcone; Escherichia coli; Anti-bacterial Activity

INTRODUCTION

Chalcones are the natural phytoconstituents widely distributed in plants originate in fruits, vegetables, grains, bark, roots, stems and flowers. The different derivatives of chalcones were synthesized from chalcones with marked biological significance such as Antibacterial, Antifungal, Antimalaria, Anti-inflammatory, Anticancer and Antitubercular activity. Hence, Chalcones are considered as an indispensable component in a variety of nutraceutical, pharmaceutical, medicinal and cosmetic applications with versatile health benefits [1-3].

In organic chemistry epoxides are valuable building blocks in the synthesis of many important reactions for derivatization. Basically for the preparation of surfactants, corrosion protection agents, additives to laundry detergents, lubricating oils, textiles and cosmetics epoxides are play important role in industry.

Present research a novel 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC: 2 to 6) series of synthetic epoxide have been synthesized. Synthesis of novel derivatives is carried out using 1-(5-chloro-2-hydroxyphenyl)-3-(2-chlorophenyl) -1-oxo-2-propene as starting material and followed by to evaluate antimicrobial activity [4,5].

MATERIALS AND METHODS

Melting points were determined in an open capillary tube and are uncorrected. IR spectra were recorded in KBr on a Perkin-Elmer spectrometer. 1H NMR spectra were recorded on a Gemini 300-MHz instrument in Dimethyl Sulfoxide (DMSO) as solvent and TMS as an internal standard. The purity of products was checked by Thin Layer Chromatography (TLC) on silica gel [6-10].

Synthesis Scheme (Figure 1)

derpharmachemica-Scheme

Figure 1: Scheme for the synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC: 2 - 6).

Synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC: 2 - 6)

Take 0.01 ml (0.293 g) of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chlorophenyl) -1-oxo-2-propene (SAC:1) and 25 ml of ethanol in a dry conical flask followed by 10 ml of 5% NaOH. Stir reaction mixture until chalcone get completely dissolved. Add 5 ml of 30% hydrogen peroxide in above reaction mixture and stir the reaction mixture for 2 Hrs. Collect the separated solid, filtered, washed with cold water and recrystallized from ethanol. All SAC: 2-6 were synthesized by same reaction mechanism (Figure 2) [11-17].

derpharmachemica-epoxy

Figure 2: Synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane

RESULTS AND DISCUSSION

Spectral Data of 1-(5-Chloro-2-hydroxyphenyl)-3-(2-chlorophenyl)-1-oxo-2,3-epoxy propane (SAC-2):
IR: ѵ max (cm-1): 3120 (OH), 1640 (C=O), 1682, 1585 (C=C aromatic).
1H NMR: δ 4.3 (d, 2H, CH), 4.45 (d, 2H, CH), 12.3 (s, 1H, OH), 7.56 (m, 3H, ArH), 7.95 (m, 4H, ArH).
Spectral Data of 1-(5-Chloro-2-hydroxy-4-methylphenyl)-3-(2-chlorophenyl)-1-oxo-2,3-epoxy propane (SAC-4):
IR: ѵ max (cm-1): 3125 (OH), 1640 (C=O), 1680, 1595 (C=C aromatic).
1H NMR:δ 4.43 (d, 2H, CH), 4.40 (d, 2H, CH), 12.35 (s, 1H, OH), 2.33 (s, 3H, CH3), 7.61 (m, 2H, ArH), 7.20 (m, 4H, ArH) (Table 1,2).

Table 1: Physicochemical data of synthesized compounds.

Sr. No. Code Molecular Formula Mol. Weight (g/mol) Yield % Melting Point (ºC) Rf-Value Appearance
1 SAC-2 C15H10O3Cl2 308 78 156 0.6 Yellow
2 SAC-3 C15H11O3Cl 274 75 152 0.82 Yellow
3 SAC-4 C16H12O3Cl2 287 79 155 0.7 Yellow
4 SAC-5 C15H11O2Cl 258 64 180 0.81 Brown
5 SAC-6 C15H10O4Cl2 324 72 162 0.8 Yellow

Table 2: The representative IR spectra and 1H NMRof synthesized compounds.

Sr. No. CODE IR (CM-1) 1H NMR
1 SAC-2 3120 (OH), 1640 (C=O), 1682, 1585 (C=C aromatic) δ 4.3 (d, 2H, CH), 4.45 (d, 2H, CH), 12.3 (s, 1H, OH), 7.56 (m, 3H, ArH), 7.95 (m, 4H, ArH).
2 SAC-4 3125 (OH), 1640 (C=O), 1680, 1595 (C=C aromatic) δ 4.43 (d, 2H, CH), 4.40 (d, 2H, CH), 12.35 (s, 1H, OH), 2.33 (s, 3H, CH3), 7.61 (m, 2H, ArH), 7.20 (m, 4H, ArH).

BIOLOGICAL SCREENING

Antibacterial Activity: The newly synthesized 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC-2 to SAC-6)were screened for antibacterial activity against Escherichia coli, Staphylococcus aureus (Pathogens obtained from animal), Xanthomonas citri and Xanthomonas malvacearum (Pathogens obtained from plant) using Disc Diffusion Method11. The Filter paper discs were soaked in solution of different compounds at concentration of 100 ppm [18-25]. The solvent aqueous DMF (5% 1ml) used for preparing solution of the compounds. The disc soaked in solution of compound placed at the center of bacteria seeded nutrient agar plates (Petri dishes). The Petri dishes were incubated at 26± 1°C for 24 hrs. The strength is reported by measuring the diameter of zone of inhibition in mm and results were standardized against tetracycline. The zone of inhibition was measured and reported in table 3.

Table 3: Biological Screening of Synthesized compound.

Sr. No. CODE Zone Inhibition in mm
Escherichia coli Staphylococcus aureus Xanthomonas malvacearum X. Citri.
1 SAC-2 14 9 14 16
2 SAC-3 12 7 11 12
3 SAC-4 18 11 24 26
4 SAC-5 15 14 17 21
5 SAC-6 21 16 19 22
6 Standard(Tetracycline) 22 26 23 24

CONCLUSION

The series of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC-2 to SAC-6) and derivatives have synthesized by conventional method and further screened for biological activity. All the compounds showed potent antibacterial activity [26-31].

ACKNOWLEDGMENT

Authors gratefully acknowledge to Raosaheb Patil Danve College of Pharmacy Badnapur, Dist. Jalna, Dr. Babasaheb Ambedkar Technological University Lonere, Raigad for providing laboratory facilities. Authors are also thankful to Principal, Teaching and Non-Teaching Members of Raosaheb Patil Danve College of Pharmacy Badnapurfor supporting in all work.

Conflict of interest statement

The authors report no conflict of interest.

REFERENCES

  1. Graham L Patrick. Oxford University press. 2006, p. 161-162.
  2. Indexed at, Google Scholar

  3. Akama T, Shida Y, Sugaya T, et al., J MedChem. 1996, 39: p. 3461-3469.
  4. Indexed at, Google Scholar, Crossref

  5. Lili Ma, Bonfield K, Amato E, et al., Bioorg Med Chem. 2012, 20: p.2603-2613.
  6. Indexed at, Google Scholar, Crossref

  7. Chulia AJ, Pouget C, Fagnere C, et al., Tetrahedron. 2000, 56: p. 6047-6052.
  8. Indexed at, Google Scholar, Crossref

  9. Brueggemeier RW, Hackett JC, Kim YW, et al., BioorgMed Chem. 2005, 13: p. 4063-4070.
  10. Indexed at, Google Scholar, Crossref

  11. Tran TD, YeonSook C, Jeong K, et al., Bioorganic Med Chem Lett. 2004, 14: p. 1165-1167.
  12. Indexed at, Google Scholar, Crossref

  13. Cotelle N, Bernier J, Catteau J, et al., Free RadBioMed. 1996, 20: p. 35- 43.
  14. Indexed at, Google Scholar, Crossref

  15. Khan MSY, Hasan SM. IJC. 2003, p. 1970-1974.
  16. Indexed at, Google Scholar        

  17. Patil SG, Utale PS, Gholse SB, et al., J Chem Pharm Res. 2012, 4: p. 501-507.
  18. Indexed at, Google Scholar        

  19. Nitin GG, Rajput PR. IntJ Pharm Bio Sci. 2102, 3: p. 389-395.
  20. Indexed at, Google Scholar        

  21. HakanGoker, David W Boykin, SulhiyeYildiz.  Bioorg Med Chem. 2005, 13: p. 1704-1714.
  22. Indexed at, Google Scholar, Crossref

  23. Kim YW, Hackett JC, Brueggemeier RW. JMed Chem. 2004, 47: p. 4032- 4040.
  24. Indexed at, Google Scholar, Crossref

  25. Yadav MR, Sabale PM, Geridhar R. Steroids. 2011, 76: p. 464- 470.
  26. Indexed at, Google Scholar, Crossref

  27. Kumar S, Pandey AK. ScientificWorldJournal. 2013, p. 1-2.
  28. Indexed at, Google Scholar, Crossref

  29. Priya k, Neha B, Robinka K. J Pharm SciPharmacol. 2014, 3: p. 2188-2216.
  30. Indexed at, Google Scholar        

  31. Serafini M, Peluso I, Raguzzini A. ProcNutr Soc. 2010, 69: p. 273-278.
  32. Indexed at, Google Scholar, Crossref

  33. Shashank K, Pandey K. ScientificWorldJournal. 2013, 16: p.162-750.
  34. Indexed at, Google Scholar, Crossref

  35. Agrawal D.  Int J Pharm Sci  nanotech. 2011, 4: p. 7-11.
  36. Indexed at, Google Scholar, Crossref

  37. Partha PR, Kunal R.  J Pharm SciPharmacol. 2010, 62: p. 1717-1728.
  38. Indexed at, Google Scholar, Crossref

  39. Virapong P, Naravut S, Chanin N, et al., Molecules. 2011, 16: p.  3597-3617.
  40. Indexed at, Google Scholar, Crossref

  41. Yujie D, Qiang W, Xiuli Z, et al.,  Eur J Med Chem. 2010, 45: p. 5612-5620.
  42. Indexed at, Google Scholar, Crossref

  43. Cavalli A, Bisi A, Bertucci C, et al., J Med Chem. 2005, 48: p. 7282-7289.
  44. Indexed at, Google Scholar, Crossref

  45. Indu AG, Punnagai M, Vasavi CS, et al., Int J Pharm Sci Res. 2014, 6: p. 141-148.
  46. Indexed at, Google Scholar        

  47. Tang G, Xiangping D, Wang Z, et al., RSC advances. 2017, p. 38171-38178.
  48. Indexed at, Google Scholar, Crossref

  49. Patel S, Shah U.  Asian J Pharm Clin Res. 2017, 10: p. 403-406.
  50. Indexed at, Google Scholar, Crossref

  51. Leonor PR, Cardenas M, Marder M, et al., Bioorg Med Chem. 2006, 14: p. 2966-2971.
  52. Indexed at, Google Scholar, Crossref

  53. Ahmed K, Murty JN, Viswanath A, et al., Bioorg Med ChemLett. 2012, 22: p. 4891-4895.
  54. Indexed at, Google Scholar, Crossref

  55. Koneni VS, Manoj K, Abdhesh K. Tetrahedron Letters. 2012, 53: p. 2355-2359.
  56. Indexed at, Google Scholar, Crossref

  57. Cutler SJ, Kabbani FM, KeaneC, et al., Eur J Med Chem. 1993, 28: p. 407-414.
  58. Google Scholar, Crossref

  59. Bano S, Javed K, Ahmed S, et al., Eur J Med Chem. 2013, 65: p. 51-59.
  60. Indexed at, Google Scholar, Crossref

  61. Patil SP. IJPBS. 2013, p.1-10.
  62. Indexed at, Google Scholar

Select your language of interest to view the total content in your interested language

30+ Million Readerbase
SCImago Journal & Country Rank
Google Scholar citation report
Citations : 23677

Der Pharma Chemica received 23677 citations as per Google Scholar report

Der Pharma Chemica peer review process verified at publons
Der Pharma Chemica- Journals on pharmaceutical chemistry