36304-47-9Relevant academic research and scientific papers
Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies
Al-Ostoot, Fares Hezam,Ara Khanum, Shaukath,Grisha, S.,Mohammed, Yasser Hussein Eissa,Vivek, H. K.,Zabiulla
, (2020/12/25)
A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.
Design, synthesis and in vitro antibacterial evaluation of naphthalen-2-yloxy based oxadiazole-2-thione derivatives
Kumar, Vivek,Kumar, Rajnish,Salahuddin,Mazumder, Avijit
, p. 266 - 270 (2021/02/02)
A series of novel Mannich bases 5-(naphthalen-2-yloxymethyl)-3-(substituted)aminomethyl-3H-[1,3,4]oxadiazole-2-thiones (5a-h) were synthesized by aminomethylation of substituted-1,3,4-oxadiazole-2(3H)-thione by equimolar concentration of primary or second
Thermally Triggered Isomerization in a Naphthalene-Based Acylhydrazone with Solid-State Optical Nonlinearity Response
Huang, Miaoling,Lin, Jinqing,Luo, Geng-Geng,Pan, Zhonghua,Qiu, Rongxing,Tao, Yunwen,Tian, Dan
supporting information, p. 4313 - 4317 (2020/12/01)
Under the assistance of the state-of-the-art meta-dynamics simulations, in this contribution, we report a push-pull-type acylhydrazone 4(Z) ([Z)-2-(naphthalen-2-yloxy)-N'-(pyridine-2-ylmethylene)acetohydrazide] connecting an electron-donating naphthalene ether group with an accepting pyridyl unit, which could be thermally converted to its configurational isomer 4(E) ([E)-2-(naphthalen-2-yloxy)-N'-(pyridine-2-ylmethylene)acetohydrazide]. The thermally triggered Z-to-E configurational isomerization not only involves up to five chemical bonds undergoing 180° rotation in the backbone of acylhydrazone, but changes the crystal packing symmetry from a centrosymmetric space group to a non-centrosymmetric one. Most impressively, the acentric crystal arrangement of 4(E) exhibits a second-harmonic generation (SHG) active response, about 2.5 times than that of KH2PO4 (KDP) standard.
Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents
Alam, Mahboob,Chavasiri, Warinthorn,Duong, Thuc-Huy,Huynh, Ngoc-Vinh,Nguyen, Huu-Hung,Nguyen, Thi-Phuong,Nguyen, Tien-Cong,Paramita Devi, Asshaima,Phan, Hoang-Vinh-Truong,Sichaem, Jirapast,Tran, Hoai-Duc,Tran, Nguyen-Minh-An
, (2020/07/10)
A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.
New oxadiazole derivatives: Synthesis and appraisal of their potential as antimicrobial agents
Dhara, Deboleena,Sunil, Dhanya,Kamath, Pooja R.,Ananda,Shrilakshmi,Balaji
, p. 21 - 30 (2018/02/14)
Introduction: The escalating threat due to dwindling effect of antibiotics and challenge of tackling rising drug-resistant infections has gathered high focus in current medicinal research. Methods: In an attempt to find new molecules that can defeat microbial resistance, two new series of 2-[2-substituted ethenyl]-5-(substituted methoxy)-1,3,4-oxadiazole derivatives were synthesized. Various aromatic hydrazides were allowed to undergo cyclization to substituted oxadiazole-2- amines in the presence of cyanogen bromide and further condensed with different heterocyclic aldehydes to give new oxadiazole derivatives. The synthesized molecules were fully characterized by various spectral techniques and tested for antimicrobial activity. Results: Almost all the newly synthesized compounds especially (5g-5l) displayed remarkable growth inhibition against three bacterial strains: M. smegmatis, S. aureus, E. coli and fungi C. albicans. The antimicrobial activity was further confirmed by MIC assay against the same microorganisms. Oxadiazole 5g displayed promising activity with a MIC value of 0.025 mM for two bacteria and fungi, whereas MIC of this compound for E. coli was 0.1 mM. Other active compounds (5h-5l) also exhibited good MIC ranging between 0.313 to 5.0 mM against the selected microorganisms. Docking simulations were generated to explore the potential binding approaches of ligand 5g at the D-alanine:d-alanine ligase (Ddl) protein of E. coli and S. aureus. Conclusion: Molecule 5g was active even at a lower concentration and could probably act as a prospective lead molecule for targeting the drug resistant microorganisms.
N - acetyl glucosamine - 1 - phosphate urea glucoside acid radical transferase inhibitors and its preparation method and application
-
, (2017/07/07)
The invention discloses an N-acetylglucosamine-1-phosphate uridyltransferase inhibitor and a preparation method thereof. The chemical structural formula of the inhibitor is as shown in the specification. The invention also discloses application of the N-acetylglucosamine-1-phosphate uridyltransferase inhibitor. The N-acetylglucosamine-1-phosphate uridyltransferase inhibitor is designed, screened an synthesized on the basis of the target enzyme activity cavity structure characteristic, has excellent selectivity and specificity and conforms to the development principle of green pesticides; besides, the inhibitory activity IC50 value of the inhibitor to the N-acetylglucosamine-1-phosphate uridyltransferase reaches up to 10 mu M, and therefore, as a lead compound, the inhibitor is worthy of further optimized synthesis and has huge potential of being further developed into novel and efficient bactericides. The inhibitor has high inhibitory activity for the N-acetylglucosamine-1-phosphate uridyltransferase and can be used as the active ingredient of a Gram-negative bacterium bactericide.
Synthesis of acylhydrazines and, symmetrical and asymmetrical diacylhydrazines from carboxylic acid via the Vilsmeier reagent mediated process
Zarei, Maaroof,Nakhli, Maliheh Eslami
, p. 1909 - 1918 (2017/02/15)
(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) has been used as an efficient and convenient reagent for the one-pot synthesis of acylhydrazines and symmetrical and asymmetrical diacylhydrazines from carboxylic acids. This reaction proceeded smoothly under mild conditions and it is quite practical, since the starting carboxylic acids can be easily handled and stored. Cleanliness, simplicity of the method and good to excellent yield of products are other advantages of this method.
One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent
Zarei, Maaroof
, p. 1867 - 1872 (2017/03/11)
A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products.
Synthesis, biological evaluation and molecular modeling study of 3,4-disubstituted 5-mercapto-1,2,4-triazoles
Sahoo, Subhas,Mahendra Kumar,Setty, C. Mallikarjuna
, p. 508 - 512 (2016/01/20)
Based on the outcome of computational docking to the active site of cytochrome P450 14α-demethylase (CYP51), diverse 3,4-disubstituted 5-mercapto-1,2,4-triazoles were prepared and screened for antioxidant and antifungal activities. The docking study of synthesized compounds showed promising binding affinity towards docked enzyme, sterol 14α-demethylase(CYP51) from trypanosome cruzi obtained from a RCSB protein data bank (PDB ID: 3KHM). The synthesized compounds were characterized by IR, 1H NMR and Mass spectral data. Among the novel synthesized compounds IV-6, IV-1 and IV-2 showed maximum antifungal activity against A. Niger and C. albicans organism when compared the standard fluconazole. For antioxidant activity, all the compounds showed moderate activity but compound IV-6 and IV-7 showed significant activity when compared to standard ascorbic acid.
Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells
Kulaba?, Necla,Tatar, Esra,Bing?l ?zakp?nar, ?zlem,?zsavc?, Derya,Pannecouque, Christophe,De Clercq, Erik,Kü?ükgüzel, ?lkay
, p. 58 - 70 (2016/08/18)
In this study, a series of thiosemicarbazide derivatives 12–14, 1,2,4-triazol-3-thione derivatives 15–17 and compounds bearing 2-(4H-1,2,4-triazole-3-ylthio)acetamide structure 18–32 have been synthesized starting from phenolic compounds such as 2-naphthol, paracetamol and thymol. Structures and purity of the target compounds were confirmed by the use of their chromatographic and spectral data besides microanalysis. All of the synthesized new compounds 12–32 were evaluated for their anti-HIV activity. Among these compounds, three representatives 18, 19 and 25 were selected and evaluated by the National Cancer Institute (NCI) against the full panel of 60 human cancer cell lines derived from nine different cancer types. Antiproliferative effects of the selected compounds were demonstrated in human tumor cell lines K-562, A549 and PC-3. These compounds inhibited cell growth assessed by MTT assay. Compound 18, 19 and 25 exhibited anti-cancer activity with IC50values of 5.96?μM (PC-3?cells), 7.90?μM (A549/ATCC cells) and 7.71?μM (K-562?cells), respectively. After the cell viability assay, caspase activation and Bcl-2 activity of the selected compounds were measured and the loss of mitochondrial membrane potential (MMP) was detected. Compounds 18, 19 and 25 showed a significant increase in caspase-3 activity in a dose-dependent manner. This was not observed for caspase-8 activity with compound 18 and 25, while compound 19 was significantly elevated only at the dose of 50?μM. In addition, all three compounds significantly decreased the mitochondrial membrane potential and expression of Bcl-2.
