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5351-23-5 Usage

Chemical Properties

white to slightly beige fine crystalline powder

Uses

Different sources of media describe the Uses of 5351-23-5 differently. You can refer to the following data:
1. 4-Hydroxybenzhydrazide is a reagent for the rapid automated determination of serum glucose.It can be used as an indicator for the determination of carbohydrates. The acid-hydrolyzable side chains of tissue (liver) bound 4-Hydroxybenzhydrazide can be used as markers to monitor its residues in chickens.
2. 4-Hydroxybenzhydrazide has been used:for determining the concentration of maltose from starch digestionfor analysis of sugars from fructan containing food hydrolysatein colorimetric assay for reducing sugar estimation from processed feedstuff

Biochem/physiol Actions

4-Hydroxybenzhydrazide (PAHBAH), is used for assaying α-amylase and glucoamylase activities. The assay based on PAHBAH measures non-specifically the free reducing sugar groups present in samples at 415nm colorimetrically.

Check Digit Verification of cas no

The CAS Registry Mumber 5351-23-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,5 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5351-23:
(6*5)+(5*3)+(4*5)+(3*1)+(2*2)+(1*3)=75
75 % 10 = 5
So 5351-23-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N2O2/c8-9-7(11)5-1-3-6(10)4-2-5/h1-4,10H,8H2,(H,9,11)

5351-23-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A12702)  4-Hydroxybenzhydrazide, 98%   

  • 5351-23-5

  • 25g

  • 293.0CNY

  • Detail
  • Alfa Aesar

  • (A12702)  4-Hydroxybenzhydrazide, 98%   

  • 5351-23-5

  • 100g

  • 768.0CNY

  • Detail
  • Alfa Aesar

  • (A12702)  4-Hydroxybenzhydrazide, 98%   

  • 5351-23-5

  • 500g

  • 3499.0CNY

  • Detail

5351-23-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Hydroxybenzhydrazide

1.2 Other means of identification

Product number -
Other names 4-hydroxybenzohydrazide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5351-23-5 SDS

5351-23-5Synthetic route

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 18h; Reflux;99%
With hydrazine hydrate In methanol for 0.05h; Microwave irradiation;94.6%
With hydrazine hydrate In ethanol for 0.2h; Reflux; Microwave irradiation;93%
C21H18Cl2N4O4
62500-75-8

C21H18Cl2N4O4

A

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

B

2-Dimethylamino-4,6-dihydrazino-sym-triazine
6476-81-9

2-Dimethylamino-4,6-dihydrazino-sym-triazine

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane for 2h; Heating;A 98%
B 55%
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water Inert atmosphere; Reflux;96%
With hydrazine hydrate In ethanol Inert atmosphere; Reflux;96%
With hydrazine hydrate In ethanol Inert atmosphere; Reflux;96%
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
Stage #1: 4-hydroxy-benzoic acid With sulfuric acid In ethanol for 6h; Reflux;
Stage #2: With hydrazine hydrate; sodium hydrogencarbonate; acetic acid Reflux;
89%
With hydrazine at 250℃; Microwave irradiation;83%
With hydrazine hydrochloride
2,4-bis(4-chlorocarbonylphenoxy)-6-methoxy-s-triazine
61370-95-4

2,4-bis(4-chlorocarbonylphenoxy)-6-methoxy-s-triazine

A

2,4‐dihydrazinyl‐6‐methoxy‐1,3,5‐triazine
19992-28-0

2,4‐dihydrazinyl‐6‐methoxy‐1,3,5‐triazine

B

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane for 2h; Heating;
C29H18Cl2N4O4
62500-77-0

C29H18Cl2N4O4

A

2-Diphenylamino-4,6-dihydrazino-sym-triazine
35968-21-9

2-Diphenylamino-4,6-dihydrazino-sym-triazine

B

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane for 2h; Heating;
4-Hydroxy-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
66996-57-4

4-Hydroxy-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

B

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

acid

acid

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2SO4 / Heating
2: hydrazine / H2O / Heating
View Scheme
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

CS2

CS2

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / H2SO4
2: 70 percent / 35percent aq. hydrazine / Ambient temperature
View Scheme
tert-butyl 2-(4-hydroxybenzoyl)hydrazinecarboxylate
521290-74-4

tert-butyl 2-(4-hydroxybenzoyl)hydrazinecarboxylate

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
deprotection;
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: manganese(IV) oxide; sodium cyanide / 24 h / 20 °C
2: hydrazine hydrate / ethanol / 3 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: iodine; potassium hydroxide / 2 h / 0 °C
2: hydrazine hydrate / ethanol / 70 °C
View Scheme
N-(4-hydroxybenzoyl)imidazole

N-(4-hydroxybenzoyl)imidazole

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 0.0166667h; Sonication;
4-hydroxybenzoyl chloride
28141-24-4

4-hydroxybenzoyl chloride

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 0.5h; Reflux;
With dmap; triethylamine; hydrazine In dichloromethane at 20℃; for 0.5h;
ethanol
64-17-5

ethanol

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
Stage #1: ethanol; 4-hydroxy-benzoic acid
Stage #2: With hydrazine hydrate for 5.25h; Reflux;
1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazole-4-carbaldehyde

1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazole-4-carbaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

(E)-N'-[{1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl}methylene]-4-hydroxybenzohydrazide

(E)-N'-[{1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl}methylene]-4-hydroxybenzohydrazide

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;100%
vanillin
121-33-5

vanillin

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N’-[(E)-(4-hydroxy-3-methoxyphenyl)methylidene]benzohydrazide

4-hydroxy-N’-[(E)-(4-hydroxy-3-methoxyphenyl)methylidene]benzohydrazide

Conditions
ConditionsYield
With acetic acid In methanol for 3h; Reflux;100%
5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N’-((5-nitrofuran-2-yl)methylene)benzohydrazide
965-52-6

4-hydroxy-N’-((5-nitrofuran-2-yl)methylene)benzohydrazide

Conditions
ConditionsYield
In water Acidic conditions; Reflux;99.8%
In ethanol for 2h; Reflux;91.4%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N’-[(E)-(4-hydroxyphenyl)methylidene]benzohydrazide
100872-56-8

4-hydroxy-N’-[(E)-(4-hydroxyphenyl)methylidene]benzohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃; for 24h;99%
With acetic acid In methanol for 2h; Reflux;96%
With acetic acid In ethanol for 3h; Reflux;90%
With acetic acid In isopropyl alcohol at 20℃; for 24h;82%
3,5-dihydroxybenzaldehyde
26153-38-8

3,5-dihydroxybenzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

(E)-N'-(3,5-dihydroxybenzylidene)-4-hydroxybenzohydrazide
1607472-21-8

(E)-N'-(3,5-dihydroxybenzylidene)-4-hydroxybenzohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃; for 24h;99%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N'-(1-phenylethyl)benzohydrazide

4-hydroxy-N'-(1-phenylethyl)benzohydrazide

Conditions
ConditionsYield
With nickel(II) triflate; 1,3-bis(dicyclohexylphosphine)propane In tert-Amyl alcohol at 120℃; for 48h; Inert atmosphere; Glovebox; Schlenk technique; Molecular sieve;99%
4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

hexakis(4-formylphenoxy)cyclotriphosphazene
77958-57-7

hexakis(4-formylphenoxy)cyclotriphosphazene

C84H66N15O18P3

C84H66N15O18P3

Conditions
ConditionsYield
In tetrahydrofuran for 18h; Reflux;98.6%
4,4′,4″‑[(1,3,5‑triazine‑2,4,6‑triyl)tris(oxy)]tribenzaldehyde
3140-75-8

4,4′,4″‑[(1,3,5‑triazine‑2,4,6‑triyl)tris(oxy)]tribenzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

2,4,6-tris[4-{(E)-[2'-(4-hydroxyphenylcarbonyl)hydrazinylidene]methyl}phenoxy]-1,3,5-triazine
1363379-35-4

2,4,6-tris[4-{(E)-[2'-(4-hydroxyphenylcarbonyl)hydrazinylidene]methyl}phenoxy]-1,3,5-triazine

Conditions
ConditionsYield
In tetrahydrofuran Reflux;98.6%
4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

salicylic acid pentafluorophenyl ester
187806-42-4

salicylic acid pentafluorophenyl ester

N-(4-hydroxybenzoyl)-N'-salicylhydrazine
41697-26-1

N-(4-hydroxybenzoyl)-N'-salicylhydrazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature;98%
Diphenylacetaldehyde
947-91-1

Diphenylacetaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

diphenylacetaldehyde p-hydroxybenzoylhydrazone
386283-90-5

diphenylacetaldehyde p-hydroxybenzoylhydrazone

Conditions
ConditionsYield
With acetic acid In ethanol for 4h; Reflux;98%
3-acetyl-4-hydroxychromen-2-one
2555-37-5

3-acetyl-4-hydroxychromen-2-one

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

3-{N-[(4'-hydroxybenzoyl)hydrazono]ethyl}-4-hydroxycoumarin

3-{N-[(4'-hydroxybenzoyl)hydrazono]ethyl}-4-hydroxycoumarin

Conditions
ConditionsYield
In propan-1-ol for 24h; Reflux;98%
4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid

N'-(4-hydroxybenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide

N'-(4-hydroxybenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide

Conditions
ConditionsYield
Stage #1: 4-hydroxybenzoic acid hydrazide; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 0.333333h;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h;
98%
3,5-diodosalicylaldehyde
2631-77-8

3,5-diodosalicylaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N'-(3,5-diiodo-2-hydroxybenzylidene)benzohydrazide

4-hydroxy-N'-(3,5-diiodo-2-hydroxybenzylidene)benzohydrazide

Conditions
ConditionsYield
In methanol for 0.5h;97%
3-acetyl-7-hydroxy-chromen-2-one
10441-27-7

3-acetyl-7-hydroxy-chromen-2-one

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

(E)-4-hydroxy-N'-(1-(7-hydroxy-2-oxo-2H-chromen-3-yl)ethylidene)benzohydrazide

(E)-4-hydroxy-N'-(1-(7-hydroxy-2-oxo-2H-chromen-3-yl)ethylidene)benzohydrazide

Conditions
ConditionsYield
With acetic acid In ethanol at 80℃; for 1h; Microwave irradiation;97%
benzo[b]thiophene-3-carboxylic acid
5381-25-9

benzo[b]thiophene-3-carboxylic acid

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

N'3-(4-hydroxybenzoyl)benzo[b]thiophene-3-carbohydrazide

N'3-(4-hydroxybenzoyl)benzo[b]thiophene-3-carbohydrazide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h;97%
sodium 2-formylbenzenesulfonate
1008-72-6

sodium 2-formylbenzenesulfonate

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

sodium 2-{(E)-[2-(4-hydroxybenzoyl)hydrazinylidene]methyl}benzenesulfonate

sodium 2-{(E)-[2-(4-hydroxybenzoyl)hydrazinylidene]methyl}benzenesulfonate

Conditions
ConditionsYield
In methanol for 2h; Reflux;97%
5-Methylfurfural
620-02-0

5-Methylfurfural

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N′-((5-methylfuran-2-yl)methylene)benzohydrazide

4-hydroxy-N′-((5-methylfuran-2-yl)methylene)benzohydrazide

Conditions
ConditionsYield
Stage #1: 4-hydroxybenzoic acid hydrazide With acetic acid In water for 0.0833333h; Sonication;
Stage #2: 5-Methylfurfural In dimethyl sulfoxide at 20℃; for 0.5h; Sonication;
97%
8-acetyl-7-hydroxycoumarin
6748-68-1

8-acetyl-7-hydroxycoumarin

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

OHC6H4C12H9O4N2

OHC6H4C12H9O4N2

Conditions
ConditionsYield
In propan-1-ol for 24h; Heating;96%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N’-[(E)-(4-methylphenyl)methylidene]benzohydrazide monomethanolate

4-hydroxy-N’-[(E)-(4-methylphenyl)methylidene]benzohydrazide monomethanolate

Conditions
ConditionsYield
acetic acid In ethanol for 4h; Heating / reflux;96%
With acetic acid In methanol for 2h; Reflux;80%
benzaldehyde
100-52-7

benzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-N’-[(E)-benzylidene]benzohydrazide

4-hydroxy-N’-[(E)-benzylidene]benzohydrazide

Conditions
ConditionsYield
With acetic acid In methanol for 2h; Reflux;96%
acetic acid In ethanol for 4h; Heating / reflux;86%
With acetic acid In isopropyl alcohol at 20℃; for 24h;62%
5-ethyl-thiophene-2-carbaldehyde
36880-33-8

5-ethyl-thiophene-2-carbaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxybenzoic acid (5-ethylthiophen-2-ylmethylene)hydrazide

4-hydroxybenzoic acid (5-ethylthiophen-2-ylmethylene)hydrazide

Conditions
ConditionsYield
acetic acid In ethanol for 4h; Heating / reflux;96%
3-bromo-5H-pyrido[3,2-b]pyrrolizin-5-one

3-bromo-5H-pyrido[3,2-b]pyrrolizin-5-one

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

N'-[3-bromo-5H-pyrido[3,2-b]pyrrolizin-5-ylidene]-4-hydroxybenzohydrazide

N'-[3-bromo-5H-pyrido[3,2-b]pyrrolizin-5-ylidene]-4-hydroxybenzohydrazide

Conditions
ConditionsYield
In ethanol for 24h; Reflux;96%
5-nitrothiophene-2-carboxaldehyde diacetate
14289-24-8

5-nitrothiophene-2-carboxaldehyde diacetate

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxy-benzoic acid [(5-nitro-thiophen-2-yl)methylene]hydrazide

4-hydroxy-benzoic acid [(5-nitro-thiophen-2-yl)methylene]hydrazide

Conditions
ConditionsYield
With sulfuric acid In ethanol; water; acetic acid95.09%
benzaldehyde
100-52-7

benzaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
In ethanol for 6h; Heating;95%
In ethanol for 4h; Reflux;76%
With sulfuric acid; acetic acid In ethanol; water Reflux;72%
With potassium hydroxide In methanol at 80℃; for 2h;
5-nitro-2-thiophenecarboxaldehyde
4521-33-9

5-nitro-2-thiophenecarboxaldehyde

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

4-hydroxybenzoic acid (5-nitrothiophen-2-ylmethylene)hydrazide

4-hydroxybenzoic acid (5-nitrothiophen-2-ylmethylene)hydrazide

Conditions
ConditionsYield
acetic acid In ethanol for 4h; Heating / reflux;95%
In ethanol; water Heating;86%
4-(4-octoxyphenyl)benzoyl chloride
62918-50-7

4-(4-octoxyphenyl)benzoyl chloride

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

C28H32N2O4
1193305-26-8

C28H32N2O4

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water at 20℃;95%

5351-23-5Relevant articles and documents

Synthesis, characterization and antioxidant activity of new dibasic tridentate ligands: X-ray crystal structures of DMSO adducts of 1,3-dimethyl-5-acetyl-barbituric acid o-hydroxybenzoyl hydrazone copper(II) complex

Giziroglu, Emrah,Aygün, Muhittin,Sarikurkcu, Cengiz,Kazar, Didem,Orhan, Nil,Firinci, Erkan,Soyleyici, H. Can,Gokcen, Ceren

, p. 199 - 205 (2013)

o-Hydroxybenzoyl hydrazine and p-hydroxybenzoyl hydrazine react with 1,3-dimethyl-5-acetyl-barbituric acid in ethanol to give H2L 1 (85% yield) and H2L2 (91% yield) respectively. The copper(II) complexes with DMSO adducts, [Cu(L 1)(DMSO)] and [Cu(L2)(DMSO)], were prepared by the stoichiometric reaction of the CuCl2·5H2O with the H2L1 and H2L2 in a molar ratio (M:L) of 1:1 in DMSO/water mixture. All compounds have been fully characterized using conventional spectroscopic techniques. X-ray structure analysis was carried out on the [Cu(L1)(DMSO)] which crystallizes in the triclinic P-1 space group. In addition, both ligands were applied several antioxidant assays including total antioxidant activity by phosphomolybdate, ferric reducing antioxidant power (FRAP) and scavenging activity on 1,1-diphenyl-2- picrylhydrazyl (DPPH). The results from antioxidant assays have shown that both ligands have excellent activities.

Seven coordinated cobalt(II) complexes with 2,6-diacetylpyridine bis(4-acylhydrazone) ligands: Synthesis, characterization, DNA-binding and nuclease activity

G?k?e, Cansu,Dilek, Nefise,Gup, Ramazan

, p. 213 - 220 (2015)

A new series of pentadentate 2,6-diacetylpyridine bis(4-acylhydrazone)s (H2L1 and H2L2) based seven-coordinated cobalt(II) complexes, [Co(Ln)X2] (n = 1 and X = DMF for (1); n = 2 and X = H2O for (2)); [Co(H2Ln)Y2] (n = 1 or 2; Y = N3- or NCS-), has been synthesized and characterized by using spectroscopic techniques. Single crystal X-ray study of [Co(L1)(DMF)2] (1) complex exhibits pentagonal-bipyramidal coordination geometry where the pentadentate N3O2 ligand in the equatorial plane of the bipyramid and two dimethylformamide molecules in the axial area. Interaction of the cobalt(II) complexes with CT DNA has been investigated by absorption titration method and viscosity measurements which reveal that the cobalt(II) complexes could bind with CT DNA through intercalation. Cleavage activity of the complexes (1) and (2) with pBR 322 plasmid DNA was evaluated by agarose gel electrophoresis demonstrating that the ability of the complexes to cleave the pBR 322 plasmid DNA via oxidative pathway, possibly due to the involvement of a diffusible hydroxyl radical mechanism in presence and absence of an oxidative agent. The nuclease activity of the Co(II) complexes has strong dependence on the concentration of complex and reaction time, both in presence and absence of hydrogen peroxide.

Seven-coordinated cobalt(II) complexes with 2,6-diacetylpyridine bis(4-hydroxybenzoylhydrazone): Synthesis, characterisation, DNA binding and cleavage properties

Gup, Ramazan,G?k?e, Cansu,Dilek, Nefise

, p. 629 - 641 (2015)

Synthesis and characterisation of three seven-coordinated cobalt(II) complexes of 2,6-diacetylpyridine bis(4-hydroxybenzoylhydrazone) (H4L) ligand, [Co(H2L)(H2O)2] (1), [Co(H4L)(N3)2] (2) and [Co(H4L)(NCS)2] (3) are described. The structures of the complexes were characterised by elemental analysis, IR, UV-vis and magnetic susceptibility measurement. The molecular structure of the [Co(H4L)(NCS)2] (3) was also determined by X-ray crystallography. Single crystal X-ray revealed that the Co(II) complex (3) has a pentagonal-bipyramidal coordination geometry, with pentadentate N3O2 ligand in the equatorial plane of the bipyramid and two isothiocyanato groups in the axial area. Interaction of the cobalt(II) complexes with CT-DNA was investigated by absorption titration method and viscosity measurements. Cleavage activity of the complexes with pBR 322 plasmid DNA was evaluated by agarose gel electrophoresis in presence and absence of an oxidative agent, and the mechanism of DNA cleavage was investigated. The results suggest that the cobalt(II) complexes bind effectively and they exhibit nuclease activity, which has strong dependence on the concentration of complex and reaction time, both in presence and absence of hydrogen peroxide.

Using m icrowave and ultrasound to synthesis of substituted bis-acyl hydrazone derivatives

Mohammed, Salim J.,Sheat, Attallah M.,A.abood, Salih,Yahya, Omar M.

, p. 6423 - 6427 (2021/11/01)

In this paper, some new bis-acyl hydrazone derivatives (4a-f) were prepared through the reaction of carboxylic acid hydrazides with 1,4-diacetylbenzene using classical methods, microwave and ultrasound irradiation methods. These compounds are obtained through a series of reactions where some carboxylic acids react with ethanol first in the presence of concentrated sulfuric acid to give the corresponding esters (2a-f), which when treatment with aqueous hydrazine give carboxylic acid hydrazides (3a-f).thus, The results proved that the use of microwave and ultrasound techniques is much better than the classical methods, as it gave a higher yield, shorter reaction time, and the absence of the use of solvents. All newly synthesized compounds were confirmed by IR, (1H & 13C) NMR spectral analysis and the corresponding reactions were monitored by TLC using the reported eluent.

Synthesis, in silico, in vitro and in vivo evaluations of isatin aroylhydrazones as highly potent anticonvulsant agents

Emami, Saeed,Valipour, Mehdi,Kazemi Komishani, Fatemeh,Sadati-Ashrafi, Fatemehsadat,Rasoulian, Maria,Ghasemian, Majid,Tajbakhsh, Mahmood,Honarchian Masihi, Patrick,Shakiba, Aidin,Irannejad, Hamid,Ahangar, Nematollah

, (2021/05/10)

In this study, a series of new isatin aroylhydrazones (5a-e and 6a-e) was synthesized and evaluated for their anticonvulsant activities. The (Z)-configuration of compounds was confirmed by 1H NMR. In vivo studies using maximal electroshock (MES) and pentylenetetrazole (PTZ) models of epilepsy in mice revealed that while most of compounds had no effect on chemically-induced seizures at the higher dose of 100 mg/kg but showed significant protection against electrically-induced seizures at the lower dose of 5 mg/kg. Certainly, N-methyl analogs 6a and 6e were found to be the most effective compounds, displaying 100% protection at the dose of 5 mg/kg. Protein binding and lipophilicity (logP) of the selected compounds (6a and 6e) were also determined experimentally. In silico evaluations of title compounds showed acceptable ADME parameters, and drug-likeness properties. Distance mapping and docking of the selected compounds with different targets proposed the possible action of them on VGSCs and GABAA receptors. The cytotoxicity evaluation of 6a and 6e against SH-SY5Y and Hep-G2 cell lines indicated safety profile of compounds on the neuronal and hepatic cells.

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