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618-94-0 Usage

Application

3-Nitrobenzhydrazide is a useful research chemical.

Check Digit Verification of cas no

The CAS Registry Mumber 618-94-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 8 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 618-94:
(5*6)+(4*1)+(3*8)+(2*9)+(1*4)=80
80 % 10 = 0
So 618-94-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H7N3O3/c8-9-7(11)5-2-1-3-6(4-5)10(12)13/h1-4H,8H2,(H,9,11)

618-94-0 Well-known Company Product Price

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  • Alfa Aesar

  • (B20800)  3-Nitrobenzhydrazide, 98+%   

  • 618-94-0

  • 5g

  • 397.0CNY

  • Detail
  • Alfa Aesar

  • (B20800)  3-Nitrobenzhydrazide, 98+%   

  • 618-94-0

  • 25g

  • 945.0CNY

  • Detail

618-94-0SDS

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 3-NITROBENZHYDRAZIDE

1.2 Other means of identification

Product number -
Other names 3-nitrobenzohydrazide

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:618-94-0 SDS

618-94-0Synthetic route

methyl 3-nitrobenzoate
618-95-1

methyl 3-nitrobenzoate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 4h; Reflux;96%
With hydrazine hydrate In ethanol at 85℃; for 4h;96.2%
With hydrazine hydrate In ethanol for 0.2h; Reflux; Microwave irradiation;95%
3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With acetic acid; acetic acid hydrazide for 0.1h; Microwave irradiation;93%
Stage #1: 3-nitrobenzoic acid With sulfuric acid In ethanol for 6h; Reflux;
Stage #2: With hydrazine hydrate; sodium hydrogencarbonate; acetic acid Reflux;
86%
Stage #1: 3-nitrobenzoic acid With potassium carbonate; dimethyl sulfate In acetonitrile at 50℃;
Stage #2: With hydrazine hydrate In methanol at 70℃;
83.02%
ethyl 3-nitrobenzoate
618-98-4

ethyl 3-nitrobenzoate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water Reflux;86%
With ethanol; hydrazine hydrate
With hydrazine hydrate In ethanol for 5h; Heating;90 % Turnov.
ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

hydrazine hydrate

hydrazine hydrate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
In ethanol for 1h; Heating;86%
1-methyl-4-nitro-5-(3-nitrobenzoyl)pyrazole
132771-14-3

1-methyl-4-nitro-5-(3-nitrobenzoyl)pyrazole

A

1-methyl-4-nitropyrazole
3994-50-1

1-methyl-4-nitropyrazole

B

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 40℃; for 0.5h;A 83%
B 78%
With hydrazine hydrate In ethanol at 40℃; for 0.5h; other substrate;A 83%
B 78%
(1H‑1,2,3‑benzotriazol‑1‑yl)(3‑nitrophenyl)methanone

(1H‑1,2,3‑benzotriazol‑1‑yl)(3‑nitrophenyl)methanone

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine In dichloromethane at 20℃; for 36h;71%
3-ethoxycarbonyl-2,6-dimethylpyridine-5-carboxylic acid 2-(m-nitrobenzoyl) hydrazide

3-ethoxycarbonyl-2,6-dimethylpyridine-5-carboxylic acid 2-(m-nitrobenzoyl) hydrazide

A

2,6-dimethyl-3,5-pyridinedicarboxylic acid dihydrazide
15420-54-9

2,6-dimethyl-3,5-pyridinedicarboxylic acid dihydrazide

B

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 5h; Heating;A n/a
B 52%
3-ethoxycarbonyl-2,6-dimethylpyridine-5-carboxylic acid 2-(m-nitrobenzoyl) hydrazide hydrochloride

3-ethoxycarbonyl-2,6-dimethylpyridine-5-carboxylic acid 2-(m-nitrobenzoyl) hydrazide hydrochloride

A

2,6-dimethyl-3,5-pyridinedicarboxylic acid dihydrazide
15420-54-9

2,6-dimethyl-3,5-pyridinedicarboxylic acid dihydrazide

B

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate Heating;
m-nitrobenzoic acid chloride
121-90-4

m-nitrobenzoic acid chloride

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / 1 h / Heating
2: hydrazine hydrate / Heating
View Scheme
With hydrazine hydrate In methanol for 0.5h; Reflux;
1-imidazolyl(3-nitrophenyl)methanone
61652-82-2

1-imidazolyl(3-nitrophenyl)methanone

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 0.0166667h; Sonication;
ethanol
64-17-5

ethanol

3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

Conditions
ConditionsYield
Stage #1: ethanol; 3-nitrobenzoic 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

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

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

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

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;100%
4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl)benzaldehyde

4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl)benzaldehyde

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

C39H50N6O4

C39H50N6O4

Conditions
ConditionsYield
In ethanol Milling; Inert atmosphere;100%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

C10H12N4O4

C10H12N4O4

Conditions
ConditionsYield
In pyridine Heating;97%
maleic anhydride
108-31-6

maleic anhydride

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

4-[N'-(3-nitro-benzoyl)-hydrazino]-4-oxo-but-2-enoic acid

4-[N'-(3-nitro-benzoyl)-hydrazino]-4-oxo-but-2-enoic acid

Conditions
ConditionsYield
for 2h; Acylation;97%
4-chloro-5-isothiocyanato-1H-indazole

4-chloro-5-isothiocyanato-1H-indazole

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

4-chloro-N-[5-(3-nitrophenyl)-1,3,4-thiadiazol-2-yl]-1H-indazol-5-amine

4-chloro-N-[5-(3-nitrophenyl)-1,3,4-thiadiazol-2-yl]-1H-indazol-5-amine

Conditions
ConditionsYield
Stage #1: 4-chloro-5-isothiocyanato-1H-indazole; 3-nitrobenzoic acid hydrazide In dichloromethane at 20℃;
Stage #2: With sulfuric acid In dichloromethane at 0 - 20℃; for 3h;
97%
4-methyl-1,2,3-thiadiazole-5-carbaldehyde
127108-66-1

4-methyl-1,2,3-thiadiazole-5-carbaldehyde

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

C11H9N5O3S

C11H9N5O3S

Conditions
ConditionsYield
In ethanol Reflux;97%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic 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'-(3-nitrobenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro isobenzofuran-5-carbohydrazide

N'-(3-nitrobenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro isobenzofuran-5-carbohydrazide

Conditions
ConditionsYield
Stage #1: 3-nitrobenzoic 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;
97%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

formylferrocene m-nitrobenzoylhydrazone

formylferrocene m-nitrobenzoylhydrazone

Conditions
ConditionsYield
In ethanol dropwise addn. of formylferrocene in anhyd. EtOH to the hydrazide in anhyd. EtOH, refluxing for 1.5 h, cooling, pptn.; filtration, washing several times with cold EtOH, drying in vac., elem. anal.;95.5%
salicylaldehyde
90-02-8

salicylaldehyde

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

salicylaldehyde N-(3-nitrobenzoyl)hydrazone
82859-78-7

salicylaldehyde N-(3-nitrobenzoyl)hydrazone

Conditions
ConditionsYield
In acetic acid at 20℃; for 0.25h; Inert atmosphere;95%
C20H15NO4S2

C20H15NO4S2

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

(S)-2-((Z)-5-(4-((E)-(2-(3-nitrobenzoyl)hydrazono)methyl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
1448801-08-8

(S)-2-((Z)-5-(4-((E)-(2-(3-nitrobenzoyl)hydrazono)methyl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid

Conditions
ConditionsYield
In ethanol at 40 - 50℃;95%
bis(carboxymethyl)trithiocarbonate
6326-83-6

bis(carboxymethyl)trithiocarbonate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

3-nitro-N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzamide

3-nitro-N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzamide

Conditions
ConditionsYield
In water for 0.5h; Reflux;95%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

3-nitrobenzoyl azide

3-nitrobenzoyl azide

Conditions
ConditionsYield
With hydrogenchloride; methylene chloride; sodium nitrite In water at 0℃;94.28%
succinic acid anhydride
108-30-5

succinic acid anhydride

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

4-[N'-(3-nitro-benzoyl)-hydrazino]-4-oxo-butyric acid

4-[N'-(3-nitro-benzoyl)-hydrazino]-4-oxo-butyric acid

Conditions
ConditionsYield
In ethyl acetate at 20℃;93%
triethyl orthobutyrate
24964-76-9

triethyl orthobutyrate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

2-(3-nitrophenyl)-5-propyl-1,3,4-oxadiazole

2-(3-nitrophenyl)-5-propyl-1,3,4-oxadiazole

Conditions
ConditionsYield
With sulfuric acid; silica gel at 20℃;93%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-(3-nitrobenzene)-1,3,4-oxadiazole
5565-72-0

2-(3-nitrobenzene)-1,3,4-oxadiazole

Conditions
ConditionsYield
With potassium aluminum sulfate at 100℃; for 6h;93%
With Al3+-K10 montmorillonite clay In neat (no solvent) at 55℃; for 0.25h; Microwave irradiation;92%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

2-(3-nitrophenyl)-5-methyl-1,3,4-oxadiazole
122733-39-5

2-(3-nitrophenyl)-5-methyl-1,3,4-oxadiazole

Conditions
ConditionsYield
With Al3+-K10 montmorillonite clay In neat (no solvent) at 55℃; for 0.25h; Microwave irradiation;93%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

trialkyl orthopropionate

trialkyl orthopropionate

2-ethyl-5-(3-nitrophenyl)-1,3,4-oxadiazole
672286-29-2

2-ethyl-5-(3-nitrophenyl)-1,3,4-oxadiazole

Conditions
ConditionsYield
With Al3+-K10 montmorillonite clay In neat (no solvent) at 55℃; for 0.25h; Microwave irradiation;93%
1,1-dichloro-2-nitro ethylene
6061-04-7

1,1-dichloro-2-nitro ethylene

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

C9H6N4O5

C9H6N4O5

Conditions
ConditionsYield
In water at 20℃; for 12h; Solvent; Green chemistry;93%
4-methylbenzoyl isothiocyanate
16794-68-6

4-methylbenzoyl isothiocyanate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

4-methyl-N-[2-(3-nitrobenzoyl)hydrazine-1-carbonothioyl]benzamide

4-methyl-N-[2-(3-nitrobenzoyl)hydrazine-1-carbonothioyl]benzamide

Conditions
ConditionsYield
In acetone at 60℃; for 2h;93%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

4-hydroxy-3-methoxy-5-((4-phenylpiperazin-1-yl)methyl)benzaldehyde
329725-00-0

4-hydroxy-3-methoxy-5-((4-phenylpiperazin-1-yl)methyl)benzaldehyde

N’-(4-hydroxy-3-methoxy-5-((4-phenylpiperazin-1-yl)methyl)benzylidene)-3-nitrobenzohydrazide

N’-(4-hydroxy-3-methoxy-5-((4-phenylpiperazin-1-yl)methyl)benzylidene)-3-nitrobenzohydrazide

Conditions
ConditionsYield
Stage #1: 3-nitrobenzoic acid hydrazide; 4-hydroxy-3-methoxy-5-[(4-phenyl-1-piperazino)-methyl]benzaldehyde With acetic acid In ethanol Reflux;
Stage #2: for 2h;
93%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

N-(m-nitrobenzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide

N-(m-nitrobenzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide

Conditions
ConditionsYield
With sulfuric acid In ethanol Heating;92%
carbon disulfide
75-15-0

carbon disulfide

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

5-(3-nitrophenyl)-1,3,4-oxadiazole-2-thiol
41421-07-2

5-(3-nitrophenyl)-1,3,4-oxadiazole-2-thiol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 20h; Reflux;92%
Stage #1: carbon disulfide; 3-nitrobenzoic acid hydrazide With potassium hydroxide In ethanol; water Reflux;
Stage #2: With hydrogenchloride In water pH=2 - 3;
80%
With potassium hydroxide In ethanol; water Reflux;66%
4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzaldehyde

4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzaldehyde

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-3-nitrobenzohydrazide

(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-3-nitrobenzohydrazide

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;92%
4-methylbenzoyl isocyanate
5843-46-9

4-methylbenzoyl isocyanate

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

C16H14N4O5

C16H14N4O5

Conditions
ConditionsYield
In toluene for 3h; Reflux;92%
Pyridine-2,6-dicarboxylic acid
499-83-2

Pyridine-2,6-dicarboxylic acid

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

2,6-bis-[5-(3-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine

2,6-bis-[5-(3-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine

Conditions
ConditionsYield
With pyridine; trichlorophosphate for 0.133333h; microwave irradiation;91%
N-ethyl-3-carbazolealdehyde
7570-45-8

N-ethyl-3-carbazolealdehyde

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

3-Nitro-benzoic acid [1-(9-ethyl-9H-carbazol-3-yl)-meth-(E)-ylidene]-hydrazide

3-Nitro-benzoic acid [1-(9-ethyl-9H-carbazol-3-yl)-meth-(E)-ylidene]-hydrazide

Conditions
ConditionsYield
for 0.1h; microwave irradiation;91%
1,1,1-trimethoxybutane
43083-12-1

1,1,1-trimethoxybutane

3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

2-(3-nitrophenyl)-5-propyl-1,3,4-oxadiazole

2-(3-nitrophenyl)-5-propyl-1,3,4-oxadiazole

Conditions
ConditionsYield
With Al3+-K10 montmorillonite clay In neat (no solvent) at 55℃; for 0.25h; Microwave irradiation;91%
3-nitrobenzoic acid hydrazide
618-94-0

3-nitrobenzoic acid hydrazide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

N'-(5-bromo-2-hydroxybenzylidene)-3-nitrobenzohydrazide
41377-50-8

N'-(5-bromo-2-hydroxybenzylidene)-3-nitrobenzohydrazide

Conditions
ConditionsYield
In ethanol91%

618-94-0Relevant articles and documents

Novel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies

?endil, K?v?lc?m,Demircio?lu, ?brahim Hakk?,Gül?in, ?lhami,Taslimi, Parham,Tokal?, Feyzi Sinan,Tuzun, Burak

, (2021/07/12)

In this study, it was aimed to synthesize novel molecules containing potential biological active phenolic Mannich base moiety and evaluate the inhibition properties against α-glycosidase (α-Gly) and acetylcholinesterase (AChE). For this purpose, phenolic aldehydes (1–3) were synthesized from 4-hydroxy-3-methoxy benzaldehyde (vanillin) according to the Mannich Reaction. Five different carboxylic acid hydrazides (4a-e) were synthesized from esters obtained from carboxylic acids. Fifteen Schiff base derivatives (5a-e, 6a-e, and 7a-e) were synthesized from the condensation reaction of compounds 1–3 with 4a-e. In this work, a series of novel Schiff bases from Phenolic Mannich bases (5a-e, 6a-e, and 7a-e) were tested toward α-Gly and AChE enzymes. Compounds 5a-e, 6a-e, and 7a-e showed Kis in ranging of 341.36 ± 31.84–904.76 ± 93.56?nM on AChE and 176.27 ± 22.87—621.77 ± 69.98?nM on α-glycosidase. Finally, novel compounds were found using molecular docking method to calculate the biological activity of these bases against many enzymes. The enzymes used in these calculations are acetylcholinesterase and α-glycosidase, respectively. Molecule 6b is more effective and active than other molecules with a docking score parameter value of ? 8.77 against AChE enzyme and 6d is more effective and active than other molecules with a docking score parameter value of ? 4.94 against α-Gly enzyme. After calculating the biological activities of novel compounds, ADME/T analysis parameters were examined to calculate the future drug use properties.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi

, (2021/05/17)

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

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Paragraph 0055-0056; 0070; 0090; 0093; 0095; 0103, (2021/07/24)

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

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