3290-99-1

Basic information

• Product Name: p-Anisohydrazide
• Synonyms: p-anisohydrazide;P-ANISIC HYDRAZIDE;P-ANISOYLHYDRAZINE;P-METHOXY BENZHYDRAZIDE;4-METHOXYBENZENE-1-CARBOHYDRAZIDE;4-METHOXYBENZOHYDRAZIDE;4-METHOXYBENZHYDRAZIDE;4-METHOXY-BENZOIC ACID HYDRAZIDE
• CAS NO: 3290-99-1
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• EINECS: 221-952-5
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Carbonyl Compounds;Hydrazides;Organic Building Blocks;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 3290-99-1.mol
• Article Data: 224

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 294.38°C (rough estimate)
• Appearance: /
• Density: 1.2265 (rough estimate)
• Refractive Index: 1.6180 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.65±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 389017
• CAS DataBase Reference: p-Anisohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: p-Anisohydrazide(3290-99-1)
• EPA Substance Registry System: p-Anisohydrazide(3290-99-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: BZ4800000
• HazardClass: IRRITANT
• Hazardous Substances Data: 3290-99-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3290-99-1 differently. You can refer to the following data:
1. 4-Methoxybenzhydrazide is used as pharmaceutical intermediates and it is also involved in a variety of organic synthesis.
2. 4-Methoxybenzhydrazide may be used to synthesize:N′-[(E)-5-bromo-2-hydroxy-3-methoxybenzylidene]-4-methoxybenzohydrazide monohydrate2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazolehydrazone ligands, which readily forms ruthenium(II) hydrazone complexes via reaction with [RuHCl(CO)(PPh3)3]

Synthesis Reference(s)

Journal of Medicinal Chemistry, 27, p. 1565, 1984 DOI: 10.1021/jm00378a007

Safety Profile

Poison by intravenous route. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits toxic fumes of Nox.

InChI:InChI=1/C8H10N2O2/c1-12-7-4-2-6(3-5-7)8(11)10-9/h2-5H,9H2,1H3,(H,10,11)

Upstream product

• 121-98-2 methyl 4-methoxybenzoate 
• 16778-84-0 4-methoxybenzoyl isothiocyanate 
• 64-17-5 ethanol 
• 7803-57-8 hydrazine hydrate 
• 100-09-4 4-methoxybenzoic acid 
• 10364-93-9 1-(4-methoxybenzoyl)-imidazole 
• 4231-69-0 1-(4-methoxybenzoyl)-1H-1,2,3-benzotriazole 
• 100-07-2 4-methoxy-benzoyl chloride 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 83511-12-0 acetic p-anisic anhydride 
• 4181-97-9 phenyl 4-methoxybenzoate 
• 3424-93-9 4-methoxyphenylacetamide 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 100724-25-2 N'-((furan-2-yl)methylene)-4-methoxybenzohydrazide 
• 109352-15-0 4-methoxy-benzoic acid-[(1-[4]pyridyl-ethylidene)-hydrazide] 
• 54019-08-8 4-methoxy-benzoic acid N'-acetyl-hydrazide 
• 51771-21-2 4-methoxy-N'-[(4-methoxyphenyl)methylidene]benzohydrazide 
• 125741-54-0 (E)-N'-(2-hydroxybenzylidene)-4-methoxybenzohydrazide 
• 6781-59-5 1-benzoyl-2-(4-methoxybenzoyl)hydrazine 
• 92555-33-4 1-(4-methoxybenzoyl)-2-(4-nitrobenzoyl)hydrazine 
• 829-35-6 2-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 99841-40-4 N'-(4-methoxy-benzoyl)-formohydrazonic acid ethyl ester 
• 3532-17-0 4-methoxybenzoyl azide 
• 51651-81-1 N-benzaldehyde(p-methoxybenzoylhydrazone) 
• 41980-89-6 4-methoxy-benzoic acid N'-thiobenzoyl-hydrazide 
• 1456-67-3 2-(4'-methoxyphenyl)-5-phenyl-1,3,4-thiadiazole 
• 99888-72-9 Succindialdehyd-bis-<4-methoxy-benzhydrazon> 

Relevant articles and documents

Design, synthesis, chemical characterization, biological evaluation, and docking study of new 1,3,4-oxadiazole homonucleoside analogs

Herein, we report the synthetic strategies and characterization of some novel 1,3,4-oxadiazole homonucleoside analogs that are relevant to potential antitumor and cytotoxic activities. The structure of all compounds is confirmed using various spectroscopic methods such as 1H-NMR, 13C-NMR, HRMS, and FTIR. These compounds were evaluated against three human cancer cell lines (MCF-7, SKBR3, and HL60 Cell Line). Preliminary investigations showed that the cytotoxic activity was markedly dependent on the nucleobase. Introduction of 5-Iodouracil 4g and theobromine 6b proved to be extremely beneficial even they were more potent than the reference drug (DOX). Also, the synthesized compounds were tested for their antiviral activities against the human varicella-zoster virus (VZV). The product 4h was (6-azauracil derivative) more potent to the reference (acyclovir) against the deficient TK ? VZV strain by about 2-fold. Finally, molecular docking suggested that the anticancer activities of compounds 6b and 4g mediated by inhibiting dual proteins EGFR/HER2 with low micromolar inhibition constant Ki range. The 1,3,4-oxadiazole homonucleosides showed a strong affinity to binding sites of target proteins by forming H-bond, carbon–hydrogen bond, Pi-anion, Pi-sulfur, Pi-sigma, alkyl, and Pi-alkyl interactions.

Efficient Synthesis of 1,4-Bis(5-aryl-1,3,4-oxadiazol-2-yl)-2,3,5,6-tetrafluorobenzenes

Abstract: An efficient acid-catalyzed condensation between substituted benzohydrazides and 2,3,5,6-tetrafluoroterephthalic acid to form 1,4-bis(5-aryl-1,3,4-oxadiazol-2-yl)-2,3,5,6-tetrafluorobenzenes is reported. The products were isolated in 74–87% yield and were characterized by 1H NMR, IR, and mass spectra.

Symmetrical heterocyclic cage skeleton: Synthesis, urease inhibition activity, kinetic mechanistic insight, and molecular docking analyses

The present study focuses on the design and synthesis of a cage-like organic skeleton containing two triazole rings jointed via imine linkage. These molecules can act as urease inhibitors. The in-vitro urease inhibition screening results showed that the combination of the two triazole skeleton in the cage-like morphology exhibited comparable urease inhibition activity to that of the reference thiourea while the metallic complexation, especially with copper, nickel, and palladium, showed excellent activity results with IC50 values of 0.94 ± 0.13, 3.71 ± 0.61, and 7.64 ± 1.21 (3a–c), and 1.20 ± 0.52, 3.93 ± 0.45, and 12.87 ± 2.11 μM (4a–c). However, the rest of compounds among the targeted series exhibited a low to moderate enzyme inhibition potential. To better understand the compounds’ underlying mechanisms of the inhibitory effect (3a and 4a) and their most active metal complexes (3b and 4b), we performed an enzymatic kinetic analysis using the Lineweaver–Burk plot in the presence of different concentrations of inhibitors to represent the non-competitive inhibition nature of the compounds, 3a, 4a, and 4b, while mixed type inhibition was represented by the compound, 3b. Moreover, molecular docking confirmed the binding interactive behavior of 3a within the active site of the target protein.

Synthesis, spectral characterization, thermal behaviour, antibacterial activity and DFT calculation on N'-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide and N'-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester

Two new compounds N'-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N'-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized and characterized with the aid of elemental analyses, IR, NMR and single crystal X-ray diffraction data. Compounds 1 and 2 crystallize in orthorhombic and monoclinic systems with space group Pna21 and P21/n, respectively. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH...π and NH...π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. Compounds 1 and 2 are thermally stable and show NLO behaviour better than the urea crystal.

Synthesis, characterization, molecular structure and self-assembly of some cobalt(III) complexes derived from diacetyl- and benzil bisaroylhydrazones

Cobalt(III) complexes of the general formula [Co(HL1-R)(L 1-R)], [Co(HL2-R)(L2-R)] and [Co(HL 1-R)2]Cl, where H2L1-R and H 2L2-R referred respectively to diacetyl and benzil bis(aroylhydrazone), have been prepared and characterized by IR, electronic, ESI and 1H NMR spectral measurements. The bisaroylhydrazone ligand in these complexes acts either as mononegative N2O tridentate, [HL 1,2-R]-, or dinegative N2O tridentate, [L 1,2-R]2-. Coordination occurs via the two diimine nitrogens and the deprotonated enolimine oxygen of one aroylhydrazone moiety, leaving the other one uncoordinated. The X-ray crystal structures of [Co(HL 2-CH3)(L2-CH3)] and [Co(HL 1-R)2]Cl (R = H, CH3) show that the molecular units are assembled into dimers through π-π stacking and hydrogen-bonded interactions respectively in the neutral and cationic complexes. Both types of dimers are linked together giving linear chains which in turn are interconnected to produce layers. These layers are further assembled with each other in [Co(HL2-CH3)(L2-CH3)] and [Co(HL1-H)2]Cl to generate three-dimensional frameworks, while in the cationic complex [Co(HL1-CH3)2]Cl, the molecular units form chains of dimers with a one-dimensional tubular structure.

Design and synthesis of pyrimidine-5-carbonitrile hybrids as COX-2 inhibitors: Anti-inflammatory activity, ulcerogenic liability, histopathological and docking studies

Two new series of 1,3,4-oxadiazole and coumarin derivatives based on pyrimidine-5-carbonitrile scaffold have been synthesized and evaluated for their COX-1/COX-2 inhibitory activity. Compounds 10c, 10e, 10h-j, 14e-f, 14i and 16 were found to be the most potent and selective inhibitors of COX-2 (IC50 0.041–0.081 μM, SI 139.74–321.95). Eight compounds were further investigated for their in vivo anti-inflammatory activity. The most active derivatives 10c, 10j and 14e displayed superior in vivo anti-inflammatory activity (% edema inhibition 39.3–48.3, 1 h; 58.4–60.5, 2 h; 70.8–83.2, 3 h; 78.9–89.5, 4 h) to the reference drug celecoxib (% edema inhibition 38.0, 1 h; 48.8, 2 h; 58.4, 3 h; 65.4, 4 h). These derivatives were also tested for their ulcerogenic liability, compound 10j showed better safety profile with reference to celecoxib while 10c and 14e exhibited mild lesions. Molecular docking studies of 10c, 10j, and 14e in the COX-2 active site revealed similar orientation and binding interactions as selective COX-2 inhibitors with a higher liability to access the selectivity side pocket.

Oxazole ring-containing honokiol thioether derivative and preparation method and application thereof

The invention discloses an oxazole ring-containing honokiol thioether derivative, a preparation method thereof and application of the oxazole ring-containing honokiol thioether derivative as an alpha-glucosidase inhibitor, the chemical structure of the oxazole ring-containing honokiol thioether derivative is shown as a general formula (I), and R is selected from non-substituted or substituted phenyl. Compared with the prior art, the invention provides the novel honokiol thioether derivative containing the oxazole ring, and the honokiol thioether derivative containing the oxazole ring has good inhibitory activity on alpha-glucosidase, provides more possibilities for treating diabetes, and is expected to be used for preparing novel candidate drug molecules for treating diabetes. In addition, the preparation process is simple, the cost is low, and the yield is high.