24310-15-4

Usage

Uses

Used in Horticulture and Agriculture:
1-(NAPHTHOXY)ACETIC ACID HYDRAZIDE is used as a plant growth regulator for enhancing the rooting of cuttings, increasing fruit set, and promoting the development of fruit and seeds. Its application in these industries is aimed at improving crop yields and quality by stimulating the growth of roots and shoots, as well as the formation of adventitious roots in cuttings.
Used in Research and Experimental Studies:
1-(NAPHTHOXY)ACETIC ACID HYDRAZIDE is utilized as a research tool to study the role of auxins in plant growth and development. This application is crucial for understanding the underlying mechanisms of plant hormone action and their impact on various physiological processes in plants.

InChI:InChI=1/C12H12N2O2/c13-14-12(15)8-16-11-7-3-5-9-4-1-2-6-10(9)11/h1-7H,8,13H2,(H,14,15)

Upstream product

• 41643-81-6 ethyl (1-naphthalenyloxy)acetate 
• 90-15-3 α-naphthol 
• 2976-75-2 1-Naphthoxyacetic acid 

Downstream Products

• 21521-02-8 5-(α-Naphthoxymethyl)-2-amino-1,3,4-oxdiazol 
• 141244-75-9 5-phenyl-1-(α-naphthyloxyacetyl)-5-hydroxy-3-(5-nitro-2-furyl)pyrazoline 
• 141244-71-5 5-(p-tolyl)-1-(α-naphthyloxyacetyl)-5-hydroxy-3-(5-nitro-2-furyl)pyrazoline 
• 141244-83-9 5-(p-chlorophenyl)-1-(α-naphthyloxyacetyl)-5-hydroxy-3-(5-nitro-2-furyl)pyrazoline 
• 325139-81-9 1-(1-naphthyloxyacetyl)-4-(4-chlorophenyloxyacetyl)-thiosemicarbazide 
• 364331-74-8 1-(1-naphthyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)thiosemicarbazide 
• 367967-11-1 1-(1-naphthyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarbazide 
• 817202-72-5 2-ethoxy-N-{N'-[(naphthalen-1-yloxy)-acetyl]-hydrazinocarbothioyl}-benzamide 
• 903762-51-6 C₁₉H₁₆ClN₃O₂S 
• 1174744-09-2 2-[3-(4-chlorophenyl)propan-3-one]-5-(1-naphthoxymethyl)-1,3,4-oxadiazole 
• 1349432-91-2 2-[3-(4-methylphenyl)-propan-3-on-1-yl]-5-(1-naphthoxymethyl)-1,3,4-oxadiazole 
• 1191246-64-6 2,6-dibromo-4-(3-((naphthalen-1-yloxy)methyl)-1,2,4-triazin-6-yl)phenol 

Relevant academic research and scientific papers

Evaluation of the anti-inflammatory and analgesic effects of Cu(II) and Zn(II) complexes derived from 2-(naphthalen-1-yloxy)-N′-(1-(pyridin-2-1) ethylidene) acetohydrazide

New Cu(II) and Zn(II) complexes of 2-(naphthalen-1-yloxy)-N′-(1- (pyridin-2-yl)ethylidene) acetohydrazide (HA2PNA) have been prepared and characterized by elemental analyses, spectral (IR, UV-visible, ESR and 1H NMR) as well as magnetic and thermal measurements. According to the data, the complexes assigned the formulae: [Cu(A2PNA)2]H 2O and [Zn(A2PNA)(OAc)(H2O)], respectively. IR data revealed that the ligand acts as before ONN and after morever ONN mononegative tridentate via deprotonated carbonyl oxygen (CO) and both (CN)imine and (CN)pyridine nitrogen atoms. The bond lengths, bond angles, HOMO, LUMO, dipole moment and charges on the atoms have been calculated by using density functional theory (DFT) at B3LYP level with 6-31G and 6-31G(d,p) basis sets to confirm the geometry of the ligand and the investigated complexes. Also, the kinetic parameters were determined for each thermal degradation stage of the complexes using Coats-Redfern and Horowitz-Metzger methods. Moreover, the complexes have been tested for anti-inflammatory and analgesic activity in rat model of collagen adjuvant arthritis and compared with piroxicam. All the compounds showed a significant anti-inflammatory and analgesic effect versus piroxicam.

Synthesis and antimicrobial activity of some heterocyclic compounds bearing benzimidazole and pyrazoline motifs

Abstract: A series of 1-(3-(1H-benzoimidazol-2-yl)-5-aryl-4-5dihydro-1H-pyrazol-1-yl)-2-(napthalene-1-yloxy)ethanones (5a–l) are synthesized and evaluated their antimicrobial activity against gram positive (S. aureus and S. pyogenes), gram negative bacteria (E. coli and P. aeruginosa), and strains of fungi (C. albicans, A. niger, and A. clavatus). Compounds were characterized by spectroscopic techniques such as 1H NMR, 13C NMR, IR, and mass spectroscopy. The newly synthesized compounds 5b, 5i and 5j, 5k showed significant antimicrobial activity against tested microorganisms. Graphical abstract: [InlineMediaObject not available: see fulltext.].

Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies

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.

Recognition of Al3+ through the off-on mechanism as a proficient driving force for the hydrolysis of BODIPY conjugated Schiff base and its application in bio-imaging

Two new BODIPY azine bearing quinoline and pyrazine attached Schiff base chemosensors (R1 and R2) have been synthesized and applied for the detection of Al3+ in CH3CN/H2O medium. Intramolecular hydrogen bonding makes both the sensors rigid and helps to encapsulate Al3+ in the cavity. The pink colour of R1 and R2 has been changed to green fluorescent upon excess addition of Al3+ which is only because of the hydrolysis of imine bond to regenerate compound 8. Another nitrogen atom present in quinoline and in pyrazine moiety made R1 and R2 more efficient in sensing of Al3+ ion compare to R1D, R2B and R2D. Cell viability and fluorescence microscopic experiments showed that the chemosensors are cytocompatible and can be used as an effective fluorescent probe for detecting Al3+ ion in the living cell.

Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents

In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.

Synthesis, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline

2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-{5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10-5 M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).

(Naphthalen-1-yloxy)-acetic acid benzylidene/(1-phenylethylidene)-hydrazide derivatives: Synthesis, antimicrobial evaluation, and QSAR studies

A series of (naphthalen-1-yloxy)-acetic acid hydrazides (1-36) was synthesized and screened, in vitro, for antibacterial, antifungal, and antiviral activities. The results of antiviral activity showed that none of the tested compounds was active against viruses at subtoxic concentrations. Further, the antimicrobial screening results demonstrated that compounds having 3,4,5-trimethoxy benzaldehyde (18), o-Br, p-CN (31), and m-NO2 acetophenone (32) substituents were the most active ones against tested strains. QSAR investigations revealed that multi-target QSAR models were effective in describing the antimicrobial activity. Springer Science+Business Media, LLC 2011.

2-[3-(4-Chloro/ethyl phenyl)propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazoles: Synthesis and biological evaluation

In the present investigation, two novel series of 2-[3-(4-chlorophenyl) propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazole and 2-[3-(4-ethylphenyl) propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazole were synthesized and tested for their antiinflammatory, analgesic, ulcerogenic and antibacterial actions. A fair number of compounds were found to have very good antiinflammatory activity in carrageenan induced rat paw edema test, while a few compounds showed significant analgesic activity in acetic acid induced writhing test. The newly synthesized compounds showed very low ulcerogenic action and moderate antibacterial action.

Synthesis and anti tuberculostatic activity of novel 1,3,4-oxadiazole derivatives

A series of novel 2,5-disubstituted 1,3,4-oxadiazole derivatives were synthesized and tested for their in vitro antimycobacterial activity. Some compounds showed interesting activity against a strain of Mycobacterium tuberculosis H37Rv. The result of the antimycobacterial activity tests revealed that 2-(2-naphthyloxymethyl)-5-phenoxymethyl-1,3,4-oxadiazole (IVd) exhibited > 90% inhibition at MIC ～6.25.

Oxadiazole mannich bases: Synthesis and antimycobacterial activity

A series of oxadiazole mannich bases were synthesized by reacting oxadiazole derivatives, dapsone and appropriate aldehyde in the presence of methanol. The synthesized compounds were evaluated for antimycobacterial activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis. Among the synthesized compounds, compound (4) 3-{2-furyl[4-(4-{2-furyl[5-(2-naphthyloxymethyl)-2-thioxo-2,3-dihydro-1,3,4-oxadiazol-3-yl]methylamino}phenylsulfonyl)anilino]methyl}-5-(2-naphthyloxymethyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione was found to be the most promising compound active against M. tuberculosis H37Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration (MIC) 0.1 μM & 1.10 μM respectively.