36304-38-8

Usage

InChI:InChI=1/C9H12N2O2/c1-7-3-2-4-8(5-7)13-6-9(12)11-10/h2-5H,6,10H2,1H3,(H,11,12)

Upstream product

• 66047-01-6 ethyl 3-methylphenoxyacetate 
• 63051-20-7 m-tolyloxyacetic acid methyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 108-39-4 3-methyl-phenol 
• 1643-15-8 2-(m-tolyloxy)acetic acid 

Downstream Products

• 21520-92-3 2-Amino-5-(3'-methylphenoxymethyl)-1,3,4-oxadiazole 
• 66178-72-1 5-m-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione 
• 372164-14-2 5-m-Tolyloxymethyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 117554-49-1 1-(3'-Methylphenoxyacetamido)-2,5-dimethylpyrrole 
• 300661-54-5 4-chloro-N-(N'-m-tolyloxyacetyl-hydrazinocarbothioyl)-benzamide 
• 372164-11-9 C₁₀H₁₃N₃O₂S 
• 817202-64-5 2-ethoxy-N-(N'-m-tolyloxyacetyl-hydrazinocarbothioyl)-benzamide 
• 1263183-61-4 C₁₄H₁₃N₃O₂S 

Relevant academic research and scientific papers

Design, modification of phyllanthone derivatives as anti-diabetic and cytotoxic agents

Twelve benzylidene derivatives, one Baeyer-Villiger oxidative, six imine derivatives were successfully designed and synthesised from phyllanthone. In the search for potential new anti-diabetic agents, phyllanthone along with its benzylidene and oxidation analogues were evaluated for enzyme inhibition against α-glucosidase. In the benzylidene series, most analogues displayed stronger activity than the mother compound. Compound 1c revealed the strongest activity, outperforming the acarbose positive control with an IC50 value of 19.59 μM. Phyllanthone and its derivatives were then tested for cytotoxic activity against the K562 cell line. The imine analogues displayed the most powerful cytotoxic activity with 3cand 3d having IC50 values of 57.55 and 68.02 μM, respectively.

N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides

A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

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.

Synthesis and Herbicidal Activity of Some Novel Pyrazole Derivatives

Some novel pyrazole derivatives were designed and synthesized through multi-step reactions from substituted phenol as starting material. Their structures were confirmed by 1H NMR, FTIR, MS and elemental analysis. All these compounds were evaluated their herbicidal activity. The preliminary bioassay results indicated that some of title compounds displayed moderate herbicidal activity at 200 μg/mL. Among them, compounds 4-chloro-N'-(2-(2,5-dimethyl-phenoxy) acetyl)-3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-N'-(2-(2,4-dichlorophenoxy)acetyl)- 3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-3-ethyl-1-methyl-N'-(2-(m-tolyloxy) acetyl)-1H-pyrazole-5-carbohydrazide and 4-chloro-3-ethyl-1-methyl-N'-(2-(3-nitrophenoxy)acetyl)- 1H-pyrazole-5-car-bohydrazide possessed 95%, 100%, 95% and 95% inhibition against Brassica campestris respectively. In the further bioassay, the compound 6l exhibited excellent herbicidal activity either monocotyledon or dicotyledon plant at 150 g/ha.

Synthesis and evaluation of antimicrobial potential of novel oxadiazoles derived from tolyloxy moiety

Oxadiazoles and m-cresol are the potent antimicrobial moieties. 2-(m-Tolyloxy)acetohydrazide (3), a derivative of ethyl-2-(m-tolyloxy)acetate), on cyclization with aromatic acids yielded 2-(aryl)-5-(m-tolyloxymethyl)- 1,3,4-oxadiazole derivatives (4a-e).

Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2- (phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives

An elevated level of blood uric acid (hyperuricemia) is the underlying cause of gout. Xanthine oxidase is the key enzyme that catalyzes the oxidation of hypoxanthine to xanthine and then to uric acid. Allopurinol, a widely used xanthine oxidase inhibitor is the most commonly used drug to treat gout. However, a small but significant portion of the population suffers from adverse effects of allopurinol that includes gastrointestinal upset, skin rashes and hypersensitivity reactions. Moreover, an elevated level of uric acid is considered as an independent risk factor for cardiovascular diseases. Therefore use of allopurinol-like drugs with minimum side effects is the ideal drug of choice against gout. In this study, we report the synthesis of a series of pyrimidin-5-one analogues as effective and a new class of xanthine oxidase inhibitors. All the synthesized pyrimidin-5-one analogues are characterized by spectroscopic techniques and elemental analysis. Four (6a, 6b, 6d and 6f) out of 20 synthesized molecules in this class showed good inhibition against three different sources of xanthine oxidase, which were more potent than allopurinol based on their respective IC50 values. Molecular modeling and docking studies revealed that the molecule 6a has very good interactions with the Molybdenum-Oxygen-Sulfur (MOS) complex a key component in xanthine oxidase. These results highlight the identification of a new class of xanthine oxidase inhibitors that have potential to be more efficacious, than allopurinol, to treat gout and possibly against cardiovascular diseases.

A rapid and high-yield synthesis of aryloxyacetyl hydrazides under microwave irradiation and with phase transfer catalysis

A series of aryloxyacetyl hydrazides 4a-l were synthesised under microwave irradiation and phase transfer catalysis conditions. By the optimisation of the reaction conditions, a rapid, high-yield and efficient method for the preparation of aryloxyacety hydrazide was given.

Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles

We have described the synthesis of new 1,2,4-triazoles and have evaluated their antimicrobial profile. Antitubercular activity was determined in triplicate using the Lowenstein-Jensen medium. A loopful of Mycobacterium tuberculosis suspension was inoculated on the surface of each Lowenstein-Jensen media containing the test compounds (100, 10 or 1 μg mL-1). To evaluate in-vitro antibacterial activity, compounds (50, 5 or 0.5 μg) were evaluated against B. subtilis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus typhi by the disc diffusion method. To evaluate antifungal activity Sabourauds Dextrose agar medium was used. Some of the compounds (5, 0.5 or 0.05 μg mL-1) were screened for activity against Aspergillus niger 88 and Aspergillus niger 90 and others were screened for activity against T. rubrum TR1, T. rubrum R6, T. rubrum R7 and T. mentagrophyte M1, using the cup plate method. Our results show that the triazoles with a pyrazine moiety at position 3 were more active as antitubercular and antifungal agents compared with the triazoles which had a pyrazine moiety at position 4 of the molecule.

Efficient one-pot synthesis of S-triazolo[3,4-b]-[1,3,5]thiadiazines containing a chiral side chain by double Mannich type reaction

An efficient and convenience method has been developed via a one-pot double Mannich type reaction for the synthesis of the important chiral s-triazole derivatives: (S)-3-α-phenylethyl-2,4-dihydro-5-aryl-oxymethyl-1,2,4-triazolo [3,4-b]-1,3,5-thiadiazines.

Synthesis and Biological Activity of 3-Pentadecylaryloxyacetic Acids, Their Hydrazides and Cyclic Derivatives: Oxadiazoles and Pyrroles

Several 3-pentadecylaryloxyacetic acids (III), their hydrazides (IV), 2-amino-5-(3'-pentadecylaryloxymethyl)-1,3,4-oxadiazoles (V) and 1-(3'-pentadecylaryloxyacetamido)-2,5-dimethylpyrroles (VI) have been synthesised and evaluated for their biological activity.Some of the compounds exhibit strong antiinflammatory action in experimental animals.Presence of a long alkyl chain (C13H31) renders the compounds to be less toxic.