72323-41-2Relevant articles and documents
In vitro α-glucosidase and α-amylase inhibitory potential and molecular docking studies of benzohydrazide based imines and thiazolidine-4-one derivatives
Gul, Zarif,Hayat, Shawkat,Hussain, Javid,Khan, Fahad,Khan, Misbah Ullah,Rahim, Fazal,Sobia,Taha, Muhammad,Uddin, Imad,Ullah, Hayat,Ullah, Munzer,Ullah, Shaheed,Zada, Hussan
, (2021/12/10)
Benzohydrazide based imine derivatives (1c-16c) and thiazolidine-4-one derivatives (1d-16d) were synthesized and characterized with different spectroscopic techniques i.e. HREI-MS, 1HNMR and 13CNMR. The synthesized analogs were examined for antidiabetic potential and hence evaluated against α-glucosidase and α-amylase enzyme. Benzohydrazide based imine derivatives showed outstanding α-glucosidase inhibition ranging from 5.60 ± 0.30 to 38.10 ± 0.30 μM when compared with acarbose (IC50 = 38.45 ± 0.80 μM). Compound 5c (IC50 = 5.60 ± 0.30 μM) has m/p-dihydroxyl groups at phenyl ring while compound 15c (IC50 = 7.30 ± 0.10 μM) has one p?hydroxyl group present at phenyl ring were most potent in the imine series. Molecular docking study further support that hydrogen bonding is predominant. Thiazolidin-4-one derivatives (1d-16d) were screen against α-amylase enzyme and were found to show excellent potential with IC50 values ranging from 0.40 ± 0.05 to 22.11 ± 1.20 μM when compared with standard acarbose (IC50 = 0.91 ± 0.20 μM). The most potent analog in the series was 5d (IC50 = 0.40 ± 0.05 μM) when compared with standard. Molecular docking study was carried out for active site determination and to rationalize the activities of the active compounds.
Synthesis and Biological Evaluation of Some Heterocyclic Compounds from Salicylic Acid Hydrazide
Sarshira,Hamada,Moghazi,Abdelrahman
, p. 1970 - 1982 (2016/11/23)
Different heterocyclic compounds were prepared starting from 2-hydroxy benzohydrazide; for example, cyclization of hydrazide hydrazone 3 derived from 2-hydroxybenzohydrazide 2 with acetic anhydride or concentrated sulfuric acid gave 1,3,4-oxadiazole derivatives 4–5. On the other hand, direct cyclization of 2-hydroxy benzohydrazide 2 with one carbon cyclizing agent gave a new derivative of 1,3,4-oxadiazole 7, 8, 9, 10, 11. Heating of hydrazide hydrazone 3 with thioglycolic acid in pyridine gave thiazolidinone 12. When 2-hydroxy benzohydrazide 2 reacted with aliphatic carboxylic acids such as formic acid or acetic acid, it gave the corresponding N-formyl or N-acetyl derivatives 6. Subsequent cyclization of 6 using phosphorous pentasulphide in pyridine gave 1,3,4-thiadiazoles 13. Cyclization of 2-hydroxy benzohydrazide with ethyl acetoacetate gives pyrazolone derivative 14. Finally, when an ethanolic solution of acid hydrazide 2 was treated with ammonium thiocyanate in 35% HCl, it gave the thiosemicarbazide 15. Subsequent treatment of 15 with concentrated sulfuric acid or 10% sodium hydroxide gave 5-amino-1,3,4-thiadiazole 16 and 1,2,4-triazole 17, respectively. The structures of all newly isolated compounds were confirmed using1H NMR, IR spectra, and elemental analyses. The antimicrobial activities for all isolated compounds were examined against different microorganisms.
Design, synthesis, and evaluation of novel small molecule inhibitors of the influenza virus protein NS1
Jablonski, Joseph J.,Basu, Dipwanita,Engel, Daniel A.,Geysen, H. Mario
experimental part, p. 487 - 497 (2012/02/15)
Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The existing vaccination program is variably effective from year to year, and drug resistance to available antivirals is a growing problem, making the development of additional antivirals an important challenge. Influenza virus non-structural protein 1 (NS1) is the centerpiece of the viral response to the host interferon (IFN) system. NS1 was demonstrated previously to be a potential therapeutic target for antiviral therapy by the identification of specific small-molecule inhibitors. One inhibitory compound, NSC125044, was subjected to chemical evaluation. Initial synthetic work comprised simplifying the core structure by removing unwanted functionality and determination of key features important for activity. Several subclasses of molecules were designed and synthesized to further probe activity and develop the basis for a structure-activity relationship. Apparent potency, as judged by activity in virus replication assays, increased dramatically for some analogs, without cytotoxicity. Results suggest that the target binding site tolerates hydrophobic bulk as well as having a preference for weakly basic substituents.
