606-26-8

Usage

Uses

Used in Organic Synthesis:
2-NITROBENZHYDRAZIDE is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and functional groups make it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Reactions:
2-NITROBENZHYDRAZIDE is used as a reagent in chemical reactions, such as the synthesis of bis-(p-nitrobenzhydrazino)-1,4-naphthoquinone through the reaction with 2,3-dichloro-1,4-naphthoquinone. This reaction demonstrates its utility in forming disubstituted products, which can be further modified or used as intermediates in the synthesis of other complex organic molecules.

Purification Methods

Crystallise the hydrazide from EtOH or EtOAc (m 120o). [Beilstein 9 H 375, 9 I 152, 9 II 246, 9 III 1481, 9 IV 1052.]

InChI:InChI=1/C7H7N3O3/c8-9-7(11)5-3-1-2-4-6(5)10(12)13/h1-4H,8H2,(H,9,11)

Upstream product

• 606-27-9 methyl 2-nitrobenzoate 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 316143-56-3 N'-isopropylidene-2-nitrobenzohydrazide 
• 304479-42-3 3-(2-nitro-benzoylhydrazono)-butyric acid ethyl ester 
• 610-34-4 ethyl 2-nitrobenzoate 

Downstream Products

• 304479-42-3 3-(2-nitro-benzoylhydrazono)-butyric acid ethyl ester 
• 16430-01-6 1-(2-nitro-benzoyl)-4,5,6,7-tetrahydro-1H-indazole 
• 6076-13-7 4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid 
• 113114-51-5 N-(N-benzoyl-L-alanyl)-N'-(2-nitro-benzoyl)-hydrazine 
• 835-14-3 N₂-(2-nitrobenzoyl)thiosemicarbazide 
• 1134-10-7 2-nitrobenzoyl azide 
• 19011-95-1 2-nitro-benzoic acid benzylidenehydrazide 
• 117522-80-2 2-nitro-benzoic acid-(4-hydroxy-benzylidenehydrazide) 
• 89898-92-0 2-(2-nitrophenyl)-1,3,4-oxadiazole 
• 103272-73-7 N'-(2-nitro-benzoyl)-formohydrazonic acid ethyl ester 
• 111589-08-3 N²,N⁴-bis-(2-nitro-benzoyl)-formohydrazidine 

Relevant academic research and scientific papers

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

COMPOUNDS AND METHODS FOR TREATING CANCER

Substituted cinnamamide compounds and analogs, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate cancer are provided.

Synthesis, antifungal and antibacterial activity of calix[4]arene-based 1,3,4-oxadiazole derivatives

We describe the synthesis of some novel p-tert-butylcalix[4]arene-based (5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate derivatives (4a–e). These compounds were synthesized by the reaction of tetra-tert-butyl calix[4]arene (1) with (5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–e) in the presence of potassium carbonate as a weak base and dry acetone as the solvent. All the newly synthesized calix[4]arene derivatives were characterized by elemental analysis and various spectroscopic methods such as FT-IR, 1H NMR,13C NMR, DEPT, and ESI-MS. The synthesized compounds were tested in vitro for their antibacterial and antifungal activities against Escherichia coli and Aspergillus fumigates in comparison with enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections. The synthesized compounds showed different inhibition zones against the tested bacteria and fungi. Compound 4c was found to be most effective against A. fumigates, whereas compound 4e was found to be equally effective against E. coli and A. fumigates.

Synthesis, characterization, and nonlinear optical properties of some new series of S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives

In the present investigation, some novel S-(5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–3e) derivatives were synthesized and their impact on optical properties was studied. They have also been characterized by elemental analysis and various spectroscopic methods including FTIR, 1 H NMR, 13 C NMR, and UV-Vis techniques. The nonlinear refractive indexes of 3a–3e were also measured in dichloromethane via Z-scan method using a continuous wave diode-pumped laser at 532 nm wavelength. The nonlinear refractive coefficient of compounds was obtained from 1011 m2/W order. Regarding the appropriate nonlinearity of these compounds, they could be considered good candidates for biooptical and photonic applications. All the synthesized compounds (3a–3e) have also been evaluated for their antimicrobial and antifungal activities. The bioactive assay showed that the synthetic compounds displayed variable inhibition zones against tested bacterium Escherichia coli and fungus Aspergillus fumigatus in comparison to enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections.

Discovery of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido) phenylurea-based thymidylate synthase (TS) inhibitor as a novel multi-effects antitumor drugs with minimal toxicity

Thymidylate synthase (TS) is a hot target for tumor chemotherapy, and its inhibitors are an essential direction for anti-tumor drug research. To our knowledge, currently, there are no reported thymidylate synthase inhibitors that could inhibit cancer cell migration. Therefore, for optimal therapeutic purposes, combines our previous reports and findings, we hope to obtain a multi-effects inhibitor. This study according to the principle of flattening we designed and synthesized 18 of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido)phenyl urea derivatives as multi-effects inhibitors. The biological evaluation results showed that target compounds could significantly inhibit the hTS enzyme, BRaf kinase and EGFR kinase activity in vitro, and most of the compounds had excellent anti-cell viability for six cancer cell lines. Notably, the candidate compound L14e (IC50 = 0.67 μM) had the superior anti-cell viability and safety to A549 and H460 cells compared with pemetrexed. Further studies had shown that L14e could cause G1/S phase arrest then induce intrinsic apoptosis. Transwell, western blot, and tube formation results proved that L14e could inhibit the activation of the EGFR signaling pathway, then ultimately achieve the purpose of inhibiting cancer cell migration and angiogenesis in cancer tissues. Furthermore, in vivo pharmacology evaluations of L14e showed significant antitumor activity in A549 cells xenografts with minimal toxicity. All of these results demonstrated that the L14e has the potential for drug discovery as a multi-effects inhibitor and provides a new reference for clinical treatment of non-small cell lung cancer.

Thiadiazoline- And pyrazoline-based carboxamides and carbothioamides: Synthesis and inhibition against nitric oxide synthase

Two new families of pyrazoline and thiadiazoline heterocycles have been developed. Their inhibitory activities against two different isoforms of nitric oxide synthase (inducible and neuronal NOS) are reported. The novel derivatives were synthesized combining the arylthiadiazoline or arylpyrazoline skeleton and a carboxamide or carbothioamide moiety, used as starting material ethyl 2-nitrobenzoates or substituted nitrobenzaldehydes, respectively. The structure-activity relationships of final molecules are discussed in terms of the R1 radical effects in the aromatic ring, the Y atom in the heterocyclic system, the X heteroatom in the main chain, and the R2 substituent in the carboxamide or carbothioamide rest. In general, thiadiazolines (5a-e) inhibit preferentially the neuronal isoform; among them, 5a is the best nNOS inhibitor (74.11% at 1 mM, IC50 = 420 M). In contrast, pyrazolines (6a-r) behave better as iNOS than nNOS inhibitors, 6m being the best molecule of this series (76.86% at 1 mM of iNOS inhibition, IC50 = 130 M) and the most potent of all tested compounds.

N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents

An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1H NMR, and 13C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents.

2-Nitrobenzohydrazide as a potent urease inhibitor: Synthesis, characterization and single crystal X-ray diffraction analysis

2-Nitrobenzohydrazide was efficiently synthesized in two steps by the esterification of 2-nitrobenzoic acid followed by the treatment with hydrazine hydrate in methanol. The structure of 2-nitrobenzohydrazide was established by modern spectro-analytical techniques including FTIR,1H and13C-NMR spectroscopy and unequivocally confirmed by single crystal X-ray diffraction data. 2-Nitrobenzohydrazide crystallized in orthorhombic space group P 21 21 21 with unit cell dimensions a = 4.9764(4) ?, b = 12.5280 (3) ?, c = 12.8512(1) ?, α = β = γ = 90°. A combination of N?H…N and N?H…O hydrogen bonds stabilized the crystal packing of 3. The synthesized compound 3 was assessed as urease inhibitor against Jack bean urease and the results revealed good inhibitory potency with an IC50 value of 4.25 ± 0.08 μM. This inhibition strength was 5-fold higher compared to the reference inhibitor thiourea (IC50 = 21.00 ± 0.11 μM). The molecular docking studies of the synthesized inhibitor 3 inside the active pocket of urease revealed several important binding interactions.

Synthesis, spectral analysis and antibacterial evaluation of 5-substituted-1,3,4-oxadiazol-2-yl 4-(4-methylpiperidin-1-ylsulfonyl)benzyl sulfides

Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio]methyl}benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4-methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, 1H-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.

Synthesis of novel 5-(aroylhydrazinocarbonyl)escitalopram as cholinesterase inhibitors

A novel series of 5-(aroylhydrazinocarbonyl)escitalopram (58–84) have been designed, synthesized and tested for their inhibitory potential against cholinesterases. 3-Chlorobenzoyl- (71) was found to be the most potent compound of this series having IC50 1.80 ± 0.11 μM for acetylcholinesterase (AChE) inhibition. For the butyrylcholinesterase (BChE) inhibition, 2-bromobenzoyl- (76) was the most active compound of the series with IC50 2.11 ± 0.31 μM. Structure-activity relationship illustrated that mild electron donating groups enhanced enzyme inhibition while electron withdrawing groups reduced the inhibition except o-NO2. However, size and position of the substituents affected enzyme inhibitions.. In docking study of AChE, the ligands 71, 72 and 76 showed the scores of 5874, 5756 and 5666 and ACE of ?64.92,-203.25 and ?140.29 kcal/mol, respectively. In case of BChE, ligands 71, 76 and 81 depicted high scores 6016, 6150 and 5994 with ACE values ?170.91, ?256.84 and ?235.97 kcal/mol, respectively.