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Year 2019, , 32 - 36, 01.06.2019
https://doi.org/10.5281/zenodo.3576583

Abstract

References

  • Alimmari, Adel SA; Marinkovi'c Aleksandar D; Mijin, Duvsan; Valentic, Natasa V; Todorovi'c Nina; Uvs'cumli'c Gordana (2010). Synthesis, structure and solvatochromic properties of 3- cyano-4, 6-diphenyl-5-(3-and 4-substituted phenylazo)-2- pyridones , Journal of the Serbian Chemical Society, 75, 1019-1032
  • Boyland, E; Gasson, JE; Williams, DC (1957). Enzyme activity in relation to cancer: The urinary $beta$-glucuronidase activity of patients suffering from malignant disease , British journal of cancer, 11, 120
  • Essa, Fadhel Omran; Kadhum, Kadhum Jwad; Abbas, A; Drea, Ali (2012). Estimation of transition state and Synthesis of Barbituric Acid with their derivatives of 1, 3, 4-Thiadiazole , Journal of Applicable Chemistry, 1, 344-351
  • Goldin, Barry R; Gorbach, Sherwood L (1976). The relationship between diet and rat fecal bacterial enzymes implicated in colon cancer , Journal of the National Cancer Institute, 57, 371-375
  • Gonick, Harvey C; Kramer, Herbert J; Schapiro, Arthur E (1973). Urinary ss-glucuronidase activity in renal disease , Archives of Internal Medicine, 132, 63-69
  • Hradec, E; Petvr'ik, R; Pezlarov'a J (1965). The activity of $beta$- glucuronidase in cases of bladder neoplasms , The Journal of urology, 94, 430-435
  • Jain, Sanjeev; Drendel, William B; Chen, Zhi-wei; Mathews, F Scott; Sly, William S; Grubb, Jeffrey H (1996). Structure of human $beta$-glucuronidase reveals candidate lysosomal targeting and active-site motifs , Nature structural biology, 3, 375
  • Khan, Khalid Mohammed; Ali, Muhammad; Farooqui, Tanveer Ahmad; Khan, Momin; Taha, Muhammad; Perveen, Shahnaz (2009). An improved method for the synthesis of 5-arylidene barbiturates using BiCl3 , J. Chem. Soc. Pak, 31, 823
  • Kidwai, Mazaahir; Thakur, Ruby; Mohan, Richa (2005). Ecofriendly synthesis of novel antifungal (thio) barbituric acid derivatives , Acta Chim Slov, 52, 88-92
  • Plum, C. (1967). Beta-glucuronidase activity in serum, cerebrospinal fluid and urine in normal subjects and in neurological and mental patients , Enzymologia biologica et clinica, 8, 97-112
  • Rahim, Fazal; Ali, Muhammad; Ullah, Shifa; Rashid, Umer; Ullah, Hayat; Taha, Muhammad; Javed, Muhammad Tariq; Rehman, Wajid; Khan, Aftab Ahmad; Abid, Obaid Ur Rahman; others (2016). Development of bis-thiobarbiturates as successful urease inhibitors and their molecular modeling studies , Chinese Chemical Letters, 27, 693-697
  • Rahim, Fazal; Malik, Fazal; Ullah, Hayat; Wadood, Abdul; Khan, Fahad; Javid, Muhammad Tariq; Taha, Muhammad; Rehman, Wajid; Rehman, Ashfaq Ur; Khan, Khalid Mohammed (2015). Isatin based Schiff bases as inhibitors of $alpha$-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies , Bioorganic chemistry, 60, 42-48
  • Ralhan, NK; Sachdev, HS (1960). Synthesis of Barbituric Acid Derivatives , J. Sci., Ind. Res, 19, 215-218
  • Ronald, Allan R; Silverblatt, Frederic; Clark, Hugh; Cutler, Ralph E; Turck, Marvin (1971). Failure of urinary beta-glucuronidase activity to localize the site of urinary tract infection , Applied and environmental microbiology, 21, 990-992
  • Schapiro, Arthur; Paul, Wellington; Gonick, Harvey (1968). Urinary beta-glucuronidase in urologic diseases of the kidneys , The Journal of urology, 100, 146-157
  • Singh, V; Khanna, R; Srivastava, VK; Palit, G; Shanker, K (1992). Synthesis and pharmacological evaluation of some phenothiazines as antidepressants , Arzneimittel-Forschung, 42, 277-280
  • Sperker, Bernhard; Backman, Janne T; Kroemer, Heyo K (1997). The role of $beta$-glucuronidase in drug disposition and drug targeting in humans , Clinical pharmacokinetics, 33, 18-31
  • Srivastava, VK; Kumar, Ashok; others (2004). Synthesis of some newer derivatives of substituted quinazolinonyl-2- oxo/thiobarbituric acid as potent anticonvulsant agents , Bioorganic & medicinal chemistry, 12, 1257-1264
  • Weissmann, Gerald; Zurier, Robert B; Spieler, Paul J; Goldstein, Ira M (1971). Mechanisms of lysosomal enzyme release from leukocytes exposed to immune complexes and other particles , Journal of Experimental Medicine, 134, 149-165
  • Zuccarello, Felice; Buemi, Giuseppe; Gandolfo, Concetta; Contino, Annalinda (2003). Barbituric and thiobarbituric acids: a conformational and spectroscopic study , Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 59, 139-151

SYNTHESIS AND MOLECULAR DOCKING STUDY OF BIS-THIOBARBITURATE DERIVATIVES AS EFFECTIVE INHIBITORS OF BETA-GLUCURONIDASE

Year 2019, , 32 - 36, 01.06.2019
https://doi.org/10.5281/zenodo.3576583

Abstract

Bis-thiobarbiturate derivatives 1-15 have been synthesized and evaluated for their in vitro βglucuronidase inhibitory potential. The structures of all compounds were confirmed throughspectroscopic techniques such as EI-MS and HNMR. Compounds 13 IC50 = 29.42 ± 0.61µM showed potent β-glucuronidase inhibitory potential better than the standard inhibitor D-saccharicacid 1, 4 lactone, IC50 = 48.4 ± 1.25 µM . The compounds 2 IC± 0.22 µM , 4 IC50 = 55.12 ± 1.13µM and 9 IC50 = 49.84 ±1.46µM showed b-glucuronidaseinhibitory potential comparable to the standard inhibitor. Compounds 1 IC50 = 68.45 ± 0.33 µM , 5 IC50 = 61.18 ± 1.42µM , 6 IC50 = 92.57 ±2.80 µM , 7 IC50 = 61.27 ± 0.45 µM , 8 IC50 = 62.85 ±0.79µM , and 12 IC50 = 77.56 ± 1.32µM also showed good inhibitory potential. The remainingcompounds are found to be completely inactive. The structure-activity relationship was establishedfor these compounds. This study identified a novel class of β-glucuronidase inhibitors

References

  • Alimmari, Adel SA; Marinkovi'c Aleksandar D; Mijin, Duvsan; Valentic, Natasa V; Todorovi'c Nina; Uvs'cumli'c Gordana (2010). Synthesis, structure and solvatochromic properties of 3- cyano-4, 6-diphenyl-5-(3-and 4-substituted phenylazo)-2- pyridones , Journal of the Serbian Chemical Society, 75, 1019-1032
  • Boyland, E; Gasson, JE; Williams, DC (1957). Enzyme activity in relation to cancer: The urinary $beta$-glucuronidase activity of patients suffering from malignant disease , British journal of cancer, 11, 120
  • Essa, Fadhel Omran; Kadhum, Kadhum Jwad; Abbas, A; Drea, Ali (2012). Estimation of transition state and Synthesis of Barbituric Acid with their derivatives of 1, 3, 4-Thiadiazole , Journal of Applicable Chemistry, 1, 344-351
  • Goldin, Barry R; Gorbach, Sherwood L (1976). The relationship between diet and rat fecal bacterial enzymes implicated in colon cancer , Journal of the National Cancer Institute, 57, 371-375
  • Gonick, Harvey C; Kramer, Herbert J; Schapiro, Arthur E (1973). Urinary ss-glucuronidase activity in renal disease , Archives of Internal Medicine, 132, 63-69
  • Hradec, E; Petvr'ik, R; Pezlarov'a J (1965). The activity of $beta$- glucuronidase in cases of bladder neoplasms , The Journal of urology, 94, 430-435
  • Jain, Sanjeev; Drendel, William B; Chen, Zhi-wei; Mathews, F Scott; Sly, William S; Grubb, Jeffrey H (1996). Structure of human $beta$-glucuronidase reveals candidate lysosomal targeting and active-site motifs , Nature structural biology, 3, 375
  • Khan, Khalid Mohammed; Ali, Muhammad; Farooqui, Tanveer Ahmad; Khan, Momin; Taha, Muhammad; Perveen, Shahnaz (2009). An improved method for the synthesis of 5-arylidene barbiturates using BiCl3 , J. Chem. Soc. Pak, 31, 823
  • Kidwai, Mazaahir; Thakur, Ruby; Mohan, Richa (2005). Ecofriendly synthesis of novel antifungal (thio) barbituric acid derivatives , Acta Chim Slov, 52, 88-92
  • Plum, C. (1967). Beta-glucuronidase activity in serum, cerebrospinal fluid and urine in normal subjects and in neurological and mental patients , Enzymologia biologica et clinica, 8, 97-112
  • Rahim, Fazal; Ali, Muhammad; Ullah, Shifa; Rashid, Umer; Ullah, Hayat; Taha, Muhammad; Javed, Muhammad Tariq; Rehman, Wajid; Khan, Aftab Ahmad; Abid, Obaid Ur Rahman; others (2016). Development of bis-thiobarbiturates as successful urease inhibitors and their molecular modeling studies , Chinese Chemical Letters, 27, 693-697
  • Rahim, Fazal; Malik, Fazal; Ullah, Hayat; Wadood, Abdul; Khan, Fahad; Javid, Muhammad Tariq; Taha, Muhammad; Rehman, Wajid; Rehman, Ashfaq Ur; Khan, Khalid Mohammed (2015). Isatin based Schiff bases as inhibitors of $alpha$-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies , Bioorganic chemistry, 60, 42-48
  • Ralhan, NK; Sachdev, HS (1960). Synthesis of Barbituric Acid Derivatives , J. Sci., Ind. Res, 19, 215-218
  • Ronald, Allan R; Silverblatt, Frederic; Clark, Hugh; Cutler, Ralph E; Turck, Marvin (1971). Failure of urinary beta-glucuronidase activity to localize the site of urinary tract infection , Applied and environmental microbiology, 21, 990-992
  • Schapiro, Arthur; Paul, Wellington; Gonick, Harvey (1968). Urinary beta-glucuronidase in urologic diseases of the kidneys , The Journal of urology, 100, 146-157
  • Singh, V; Khanna, R; Srivastava, VK; Palit, G; Shanker, K (1992). Synthesis and pharmacological evaluation of some phenothiazines as antidepressants , Arzneimittel-Forschung, 42, 277-280
  • Sperker, Bernhard; Backman, Janne T; Kroemer, Heyo K (1997). The role of $beta$-glucuronidase in drug disposition and drug targeting in humans , Clinical pharmacokinetics, 33, 18-31
  • Srivastava, VK; Kumar, Ashok; others (2004). Synthesis of some newer derivatives of substituted quinazolinonyl-2- oxo/thiobarbituric acid as potent anticonvulsant agents , Bioorganic & medicinal chemistry, 12, 1257-1264
  • Weissmann, Gerald; Zurier, Robert B; Spieler, Paul J; Goldstein, Ira M (1971). Mechanisms of lysosomal enzyme release from leukocytes exposed to immune complexes and other particles , Journal of Experimental Medicine, 134, 149-165
  • Zuccarello, Felice; Buemi, Giuseppe; Gandolfo, Concetta; Contino, Annalinda (2003). Barbituric and thiobarbituric acids: a conformational and spectroscopic study , Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 59, 139-151
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Details

Primary Language English
Journal Section Research Article
Authors

Hayat Ullah This is me

Fahad Khan This is me

Fazal Rahim This is me

Zia Ur Rehman This is me

Muhammad Taha This is me

Abdul Wadood This is me

Fawad Ahmad This is me

Zainul Wahab This is me

Imad Uddin This is me

Khalid Zaman This is me

Publication Date June 1, 2019
Published in Issue Year 2019

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