107095-39-6

Upstream product

• 644-78-0 2-hydroxychalcone 
• 98-86-2 acetophenone 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 644-78-0 2-hydroxychalcone 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 

Downstream Products

• 140473-01-4 (4-Bromo-phenyl)-(2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-4-yl)-methanone 
• 140472-99-7 Biphenyl-4-yl-(2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-4-yl)-methanone 
• 140473-09-2 C₂₅H₃₀N₂O 
• 140472-90-8 4-Ethyl-2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalene 
• 140472-93-1 4-(4-Bromo-phenyl)-2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalene 
• 1149372-34-8 4-[5-(2-hydroxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-2(5H)-one 
• 1149372-40-6 2-[5-(2-hydroxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one 
• 140473-03-6 4,4-Dimethyl-2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalene 
• 140472-95-3 Dimethyl-[4-(2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-4-yl)-phenyl]-amine 
• 140473-05-8 4-Methyl-2,4-diphenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalene 
• 140472-97-5 2-Phenyl-4-((E)-styryl)-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalene 
• 140473-07-0 C₂₀H₂₀N₂O 
• 140473-00-3 (4-Chloro-phenyl)-(2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-4-yl)-methanone 

Relevant academic research and scientific papers

Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies

In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.

Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds

A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.

Design, synthesis and biological evaluation of tricyclic pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one scaffolds as selective BuChE inhibitors

Based on the structural analysis of tricyclic scaffolds as butyrylcholinesterase (BuChE) inhibitors, a series of pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one derivatives were designed, synthesized and evaluated for their acetylcholinesterase (AChE) and BuChE inhibitory activity. Compounds with 5-carbonyl and 7- or/and 9-halogen substitutions showed potential BuChE inhibitory activity, among which compounds 6a, 6c and 6g showed the best BuChE inhibition (IC50 = 1.06, 1.63 and 1.63 μM, respectively). The structure–activity relationship showed that the 5-carbonyl and halogen substituents significantly influenced BuChE activity. Compounds 6a and 6g were found nontoxic, lipophilic and exhibited remarkable neuroprotective activity and mixed-type inhibition against BuChE (Ki = 7.46 and 3.09 μM, respectively). Docking studies revealed that compound 6a can be accommodated into BuChE via five hydrogen bonds, one Pi–Sigma interaction and three Pi–Alkyl interactions.

Novel tricyclic pyrazolo[1,5-d][1,4]benzoxazepin-5(6H)-one: Design, synthesis, model and use as hMAO-B inhibitors

Based on our recently reported selective hMAO-A inhibitors, on which, the intramolecular cyclization led to a very interesting change of isoform selectivity. A series of selective hMAO-B inhibitors (3a-3u) with novel scaffold of tricyclic pyrazolo[1,5-d][1,4]benzoxazepin-5(6H)-one were designed and synthesized. Compound 3u (IC50 = 221 nM) exhibited the best inhibitory activity and isoform selectivity against hMAO-B, superior to selegiline (IC50 = 321 nM), which is a commercial selective hMAO-B inhibitor used to Parkinson's disease. Modeling study indicated that the selectivity of our compounds to hMAO-B is determined by at least two residues, i.e., Ile 199 and Cys 172 (or corresponded Phe 208 and Asn 181 of hMAO-A). These data support further studies to assess rational design of more efficiently selective hMAO-B inhibitors.

Design and synthesis of novel 2-pyrazoline-1-ethanone derivatives as selective MAO inhibitors

Thirty seven novel 2-pyrazoline-1-ethanone derivatives were designed, synthesized and evaluated as selective hMAO inhibitors. Among them, compounds 7h (IC50 = 2.40 μM) and 12c (IC50 = 2.00 μM) exhibited best inhibitory activity and selectivity against hMAO-A, surpassing that of the positive control Clorgyline (IC50 = 2.76 μM). Based on selective activity of hMAO-A, SAR analysis showed that the order of N1 substituent contribution was bromo (3) > piperidinyl (4) > morpholinyl (5) > imidazolyl (6), and compounds with electron-withdrawing substituents (-F, -Cl) at C3 or C5 phenyl ring of 2-pyrazoline nucleus dedicated stronger MAO-A inhibitory activity. Molecular docking showed that compounds 7h and 12c were nicely bound to hMAO-A via two hydrogen bonds (SER209, GLU216), one Pi-Pi interaction and three hydrogen bonds (SER209, GLU216, TYR69), one Sigma-Pi interaction, respectively. In addition, the substituent at C3 position of 2-pyrazoline with the N1 acetyl has little effect on MAO-A inhibitory activity. These data support further studies to assess rational design of more efficiently selective hMAO inhibitors in the future.

Synthesis of new 4-thiazolidinone-, pyrazoline-, and isatin-based conjugates with promising antitumor activity

The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1, 3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1-23 and 3-(3,5-diarylpyrazol- 1-yl)-2,3-dihydro-1H-indol-2-ones 24-39 are performed. I

Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies

Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (5-16) were found to be potent inhibitors of hMAO-A isoform with SIMAO-A/

Pyrazoline-based mycobactin analogues as MAO-inhibitors

3,5-Diaryl carbothioamide pyrazolines designed as mycobactin analogs (mycobacterial siderophore) were reported to be potent antitubercular agents under iron limiting condition in our earlier study. Clinical complications of newly introduced antibiotic Linezolid, due its MAO inhibitory activity, prompted us to evaluate our compounds for their MAO-inhibitory activity against rat liver MAO-A and MAO-B as pyrazolines were reported to be antidepressants and MAO inhibitors. The present study carried out with this pilot library of 32 compounds will provide us with necessary information for designing antitubercular molecules with reduced MAO-inhibitory activity and also help us in identifying a selective MAO-B inhibitor which has potential clinical utility in neurodegenerative disorders. Thirty-two compounds analyzed has shown spectrum of activity from selective to nonselective against two isoforms of rat liver MAO-A and MAO-B and also as competitive, reversible to non-competitive, irreversible. It is also interesting to note that anti-tubercular compound 11, 14 and 16 were also found to be selective inhibitors of rat liver MAO-B. Docking studies with human MAO shows that compound 11 interacts with the catalytic site of both the isoforms, suggesting compound 11 as nonselective inhibitor of human MAO isoforms.

Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis

Drugs inhibiting the iron scarcity-induced, siderophore-mediated iron-scavenging systems of Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) may provide new therapeutic lines of defense. Compounds with structural similarities to siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions, which mimic the iron scarcity these pathogens encounter and must adapt to in the host, and under standard iron-rich conditions for comparison. New antimicrobials were identified, some of which warrant exploration as initial leads against potentially novel targets and small-molecule tools to assist in the elucidation of targets specific to iron-scarcity adapted Mtb and Yp.

Synthesis of some novel 2,3,4,8,9-pentahydro-7-(4-haloaryl)-pyrazolo[5,1-e] benzo[1,5]oxazocines and 2,3(erythro), 7,8-tetrahydro-2-aryl-3-(4-fluoro-3- methylbenzoyl)-6-(4-haloaryl)pyrazolo[5,1-d] benzo[1,4]oxazepines via solid-liquid PTC

In this communication, a simple and straightforward procedure for the heterocyclization of 1H-4,5-dihydro-3-(4-haloaryl)-5-substituted phenylpyrazoles (4) with 1-bromo-3-chloropropane and 2,3-dibromo-1-(4-fluoro-3-methylphenyl)-3- phe- nylpropanone affording 2,3,4,8,9-pentahydro-7-(4-haloaryl)pyrazolo[5,1-e] benzo[1,5] oxazocines 5 and regioselective synthesis of 2,3(erythro),7,8- tetrahydro-2- aryl-3-(4-fluoro-3-methylbenzoyl)-6-(4-halophenyl)pyrazolo[5,1-d] benzo[1,4]oxa- zepines 6, respectively, via solid-liquid PTC is reported. All the synthesized compounds have been characterized on the basis of their spectral studies (IR, PMR, and MS) and analytical data. Copyright Taylor & Francis Group, LLC.