67067-01-0

Basic information

• Product Name: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID HYDRAZIDE
• Synonyms: 2-(4-oxo-3,4-dihydroquinazolin-3-yl)acetohydrazide
• CAS NO: 67067-01-0
• Molecular Formula: C₁₀H₁₀N₄O₂
• Molecular Weight: 218.21
• Mol File: 67067-01-0.mol

Chemical Properties

• Appearance: /
• Density: 1.47g/cm³
• Refractive Index: 1.699
• CAS DataBase Reference: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID HYDRAZIDE(67067-01-0)
• EPA Substance Registry System: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID HYDRAZIDE(67067-01-0)

Safety Data

• Hazardous Substances Data: 67067-01-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10N4O2/c11-13-9(15)5-14-6-12-8-4-2-1-3-7(8)10(14)16/h1-4,6H,5,11H2,(H,13,15)

Upstream product

• 16347-69-6 2-(4-oxo-(4H)-quinazoline-3-yl)acetate ethyl ester 
• 134-20-3 2-carbomethoxyaniline 
• 491-36-1 4-Hydroxyquinazoline 
• 118-92-3 anthranilic acid 

Downstream Products

• 465504-66-9 C₁₈H₁₆N₄O₂ 
• 67140-53-8 C₁₇H₁₃FN₄O₂ 
• 67140-54-9 C₁₇H₁₃ClN₄O₂ 
• 67140-57-2 C₁₇H₁₃N₅O₄ 
• 155914-22-0 C₁₇H₁₄N₄O₂ 
• 307544-14-5 N'-(4-methoxybenzylidene)-2-(4-oxoquinazolin-3(4H)-yl)-acetohydrazide 
• 307544-16-7 C₁₉H₁₈N₄O₄ 
• 1184752-22-4 C₁₇H₁₂Cl₂N₄O₂ 

Relevant articles and documents

Synthesis of some new quinazolin-4(3H)-one derivatives and evaluation of their anticonvulsant activity

We reported the synthesis of a novel series of quinazolin-4(3H)-one derivatives bearing oxadiazole, thiadiazole, and other moieties in the 3-position of the quinazolinone nucleus using appropriate synthetic route. The compounds were evaluated for their anticonvulsant activity using picrotoxin model, GABA-A receptor antagonist. Five compounds showed significantly prolonged times for convulsions compared with the standard drug phenobarbital. Graphical abstract: [Figure not available: see fulltext.]

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

Novel (Z)-N'-(2-oxoindolin-3-ylidene)-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides and an anticancer composition comprising the same as an active ingredient

(Z)- N' - (2-oxoindolin -3 - ylidene) -2 - (4-oxoquinazolin -3 (4H) - yl) acetohydrazide and an anticancer composition containing the same as an active ingredient. , It will be described below. (Z)- N' - (2-oxoindoline -3 - ylidene) -2 - (4-oxazoline -3 (4H) - yl) acetohydrazide according to the present invention activates procacaspase -3 to promote the conversion to caspase -3, so that it can be used as a proliferation inhibitor for various cancer cells. The compound according to the present invention can be developed as an active ingredient of a potent anticancer agent.

New Acetohydrazides Incorporating 2-Oxoindoline and 4-Oxoquinazoline: Synthesis and Evaluation of Cytotoxicity and Caspase Activation Activity

In our search for new small molecules activating procaspase-3, we have designed and synthesized a series of new acetohydrazides incorporating both 2-oxoindoline and 4-oxoquinazoline scaffolds. Biological evaluation showed that a number of these acetohydrazides were comparably or even more cytotoxic against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI?H23, lung cancer) in comparison to PAC-1, a first procaspase-3 activating compound, which was used as a positive control. One of those new compounds, 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N′-[(3Z)-5-methyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene]acetohydrazide activated the caspase-3 activity in U937 human lymphoma cells by 5-fold higher than the untreated control. Three of the new compounds significantly induced necrosis and apoptosis in U937 cells.

(E)-N'-Arylidene-2-(4-oxoquinazolin-4(3H)-yl) acetohydrazides: Synthesis and evaluation of antitumor cytotoxicity and caspase activation activity

In our search for novel small molecules activating procaspase-3, we have designed and synthesised a series of novel acetohydrazides incorporating quinazolin-4(3H)-ones (5, 6, 7). Biological evaluation revealed eight compounds with significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5t displayed cytotoxicity up to 5-fold more potent than 5-FU. Analysis of structure-activity relationships showed that the introduction of different substituents at C-6 position on the quinazolin-4(3H)-4-one moiety, such as 6-chloro or 6-methoxy potentially increased the cytotoxicity of the compounds. In term of caspase activation activity, several compounds were found to exhibit potent effects, (e.g. compounds 7 b, 5n, and 5l). Especially, compound 7 b activated caspases activity by almost 200% in comparison to that of PAC-1. Further docking simulation also revealed that this compound potentially is a potent allosteric inhibitor of procaspase-3.

Novel 3,4-dihydro-4-oxoquinazoline-based acetohydrazides: Design, synthesis and evaluation of antitumor cytotoxicity and caspase activation activity

In search for novel small molecules with antitumor cytotoxicity via activating procaspase-3, we have designed and synthesized three series of novel (E)-N′-benzylidene-4-oxoquinazolin-3(4H)-yl)acetohydrazides (5a-j, 6a-h, and 7a-h). On the phenyl ring ò the benzylidene part, three different substituents, including 2-OH-4-OCH3, 4-OCH3, and 4-N(CH3)2, were introduced, respectively. Biological evaluation showed that the acetohydrazides in series 5a-j, in which the phenyl ring of the benzylidene part was substituted by 2-OH-4-OCH3 substituent, exhibited potent cytotoxicity against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI-H23, lung). Most of the compounds, in this series, especially compounds 5c, 5b and 5h, also significantly activated caspase-3 activity. Among these, compound 5c displayed 1.61-fold more potent than PAC-1 as caspase-3 activator. Cell cycle analysis showed that compounds 5b, 5c, and 5h significantly arrested the cell cycle in G1 phase. Further apoptotic studies also demonstrated compounds 5b, 5c, and 5h as strong apoptotic cell death inducers. The docking simulation studies showed that these compounds could activate procaspase via chelating Zn2+ ion bound to the allosteric site of the zymogen.

A NOVEL QUINAZOLINE-BASED ACETOHYDRAZIDE AS A PROCASPASE-3 ACTIVATOR AND AN ANTICANCER COMPOSITION COMPRISING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a novel quinazoline-based acetohydrazide as an activator of procaspase-3 and an anticancer composition comprising the same as an active component. Specifically, a novel quinazoline-based acetohydrazide derivative according to the present invention activates procaspase-3 to promote the conversion to caspase-3, thereby being able to be used as a proliferation inhibitor for various cancer cells. A compound according to the present invention is expected to be developed as an active component of potent anticancer agents.COPYRIGHT KIPO 2020

Containing 1, 2, 4 - triazole thioether quinazoline ketone compound and its synthetic method and application

The invention discloses a quinazolinone compound containing 1, 2, 4-triazole thioether and synthesizing method and application of quinazolinone compound. The quinazolinone compound for preventing and curing plant pathogens is indicated by the general formula (I). Methyl anthranilate, formamide, ethyl bromoacetate, hydrazine hydrate, phenyl isothiocyanate, substitution benzyl halide or 2-chlorine-5 chloromethyl pyridine is used as raw material and subjected to six-step reaction to synthesize the target compound. The quinazolinone compounds A7, A8 and A19 are good in inhibitory activity on rice bacterial leaf blight germs. The quinazolinone compound A19 is good in inhibitory activity on citrus canker germs. The inhibitory activity on wheat scab germs of the quinazolinone compounds A14 and A18 and the inhibitory activity on apple rotting germs of the quinazolinone compound A8 are equal to that of control chemical hymexazol.

Synthetic method and application of quinazolinone compounds containing 1,2,4-triazolethione Schiff base

The invention discloses a preparation method and a bacteriostatic activity of plant pathogen prevention and treatment compounds quinazolinone compounds containing a 1,2,4-triazolethione Schiff base, and concretely relates to compounds represented by general formula (I), and a preparation method thereof. The quinazolinone target compounds containing the 1,2,4-triazolethione Schiff base are synthesized from methyl ortho-aminobenzoate, methanamide, ethyl bromoacetate, hydrazine hydrate, carbon disulfide, potassium hydroxide and aromatic aldehyde through the steps of ring closure, alkylation, hydrazinolysis, salt formation, ring closure and a Schiff base reaction. Compounds F11 and F19 have better Xanthomonas oryzae and Xanthomonas axonopodis pv. citri inhibition activity than a contrast medicate bismerthiazol under 200mg/mL or 100mg/mL; and the synthesized compounds have medium to excellent Sclerotinia scleotiorum inhibition activity, and compounds F4, F5, F6, F8, F9, F17 and F25 have broad-spectrum inhibition activity on six test fungi.

Synthesis and biological activities of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety

A series of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety were synthesised and their antimicrobial activities were evaluated. All the target compounds were characterised by 1H NMR, 13C NMR, ESI-MS, IR and elemental analyses. The single crystal structure of 3-((5-((2-fluorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIi) was also determined. The preliminary bioassays indicated that some of the target compounds possessed good antimicrobial activities. For example, 3-((4-phenyl-5-((4-(trifluoromethyl)benzyl)thio)-4H- 1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIs) exhibited the best inhibitory effect against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri with the half-effective concentration (EC50) values of 47.6 μg mL-1 and 22.1 μg mL-1, respectively, which were superior to the commercial bactericide, bismerthiazol. Meanwhile, 3-((5-((4-chlorobenzyl)thio)-4-phenyl-4H- 1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIh) exhibited better fungicidal activities against Pellicularia sasakii and Colletotrichum capsici at the concentration of 50 μg mL-1, in comparison with the commercial fungicide, hymexazol.