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14529-12-5

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14529-12-5 Usage

Description

6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione is a benzoxazine derivative with the molecular formula C9H6ClNO3. It is characterized by the presence of a chlorine atom and a methyl group, which may contribute to its unique chemical and biological properties. As a member of the benzoxazine family, it has potential applications in various fields, particularly in the pharmaceutical industry, due to the known antimicrobial, anti-inflammatory, and anticancer properties of benzoxazine derivatives.

Uses

Used in Pharmaceutical Industry:
6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione is used as a potential active pharmaceutical ingredient for its antimicrobial, anti-inflammatory, and anticancer properties. The presence of the chlorine and methyl groups may enhance its effectiveness in these applications, although further research and testing are required to fully understand its potential uses and effects.
Used in Antimicrobial Applications:
6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione is used as an antimicrobial agent in the pharmaceutical industry, leveraging its ability to inhibit the growth of various microorganisms. The chlorine atom and methyl group may contribute to its potency and selectivity against specific pathogens.
Used in Anti-inflammatory Applications:
In the pharmaceutical industry, 6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione is used as an anti-inflammatory agent, potentially reducing inflammation and associated symptoms. The unique structure of this compound may provide a novel approach to managing inflammatory conditions.
Used in Anticancer Applications:
6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione is used as an anticancer agent in the pharmaceutical industry, with potential to target and inhibit the growth of cancer cells. The presence of the chlorine and methyl groups may enhance its ability to interfere with cancer cell proliferation and survival pathways.
Note: The specific applications and their reasons are inferred from the general properties of benzoxazine derivatives and the presence of chlorine and methyl groups in the compound. Further research is necessary to validate these potential uses and to explore additional applications in different industries.

Check Digit Verification of cas no

The CAS Registry Mumber 14529-12-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,5,2 and 9 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 14529-12:
(7*1)+(6*4)+(5*5)+(4*2)+(3*9)+(2*1)+(1*2)=95
95 % 10 = 5
So 14529-12-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H6ClNO3/c1-11-7-3-2-5(10)4-6(7)8(12)14-9(11)13/h2-4H,1H3

14529-12-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-chloro-1-methyl-3,1-benzoxazine-2,4-dione

1.2 Other means of identification

Product number -
Other names 5-CHLORO-N-METHYLISATOIC ANHYDRIDE

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:14529-12-5 SDS

14529-12-5Synthetic route

5-Chloroisatoic anhydride
4743-17-3

5-Chloroisatoic anhydride

methyl iodide
74-88-4

methyl iodide

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
In ice-water; ISOPROPYLAMIDE90%
With sodium carbonate In N,N-dimethyl-formamide85.2%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;83%
carbon monoxide
201230-82-2

carbon monoxide

N-methyl(p-chloroaniline)
932-96-7

N-methyl(p-chloroaniline)

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
With oxygen; copper diacetate; palladium diacetate; potassium iodide; Trimethylacetic acid In acetonitrile at 60℃; under 760.051 Torr; regioselective reaction;78%
5-Chloroisatoic anhydride
4743-17-3

5-Chloroisatoic anhydride

methyl bromide
74-83-9

methyl bromide

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
Stage #1: 5-Chloroisatoic anhydride With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: methyl bromide In N,N-dimethyl-formamide for 18h;
72%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;
carbon monoxide
201230-82-2

carbon monoxide

4-chloro-N,N-dimethylaniline
698-69-1

4-chloro-N,N-dimethylaniline

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); oxygen; copper diacetate In N,N-dimethyl-formamide; toluene at 100℃;71%
With dichloro bis(acetonitrile) palladium(II); oxygen; copper diacetate In N,N-dimethyl-formamide; toluene at 100℃; under 760.051 Torr; for 24h;71%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

dimethyl sulfate
77-78-1

dimethyl sulfate

5-chloroanthranilic acid
635-21-2

5-chloroanthranilic acid

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
(i) aq. NaOH, (ii) /BRN= 385653/, (iii) AcCl; Multistep reaction;
5-Chloroisatoic anhydride
4743-17-3

5-Chloroisatoic anhydride

CH3-Hal

CH3-Hal

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
With sodium hydride 1.) DMF, 2 h, 2.) 8 h; Multistep reaction;
5-Chloroisatoic anhydride
4743-17-3

5-Chloroisatoic anhydride

methyl halide

methyl halide

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
(i) NaH, AcNMe2, (ii) methyl halide; Multistep reaction;
5-chloro-1-methylindoline-2, 3-dione
60434-13-1

5-chloro-1-methylindoline-2, 3-dione

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;
N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide
65798-06-3, 17122-56-4

N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2SO4 / 80 °C
2: NaH / N,N-dimethyl-acetamide / 20 °C
3: mCPBA / CH2Cl2 / 20 °C
View Scheme
5-chloroindole 2,3-dione
17630-76-1

5-chloroindole 2,3-dione

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaH / N,N-dimethyl-acetamide / 20 °C
2: mCPBA / CH2Cl2 / 20 °C
View Scheme
4-chloro-aniline
106-47-8

4-chloro-aniline

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NH2OH*HCl; Na2SO4; aq. conc. HCl / Heating
2: H2SO4 / 80 °C
3: NaH / N,N-dimethyl-acetamide / 20 °C
4: mCPBA / CH2Cl2 / 20 °C
View Scheme
5-chloroanthranilic acid
635-21-2

5-chloroanthranilic acid

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 20 - 100 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: 1,2-dichloro-ethane / 4 h / Reflux
2: N,N-dimethyl-formamide / 18 h / 20 °C / Alkaline conditions
View Scheme
Multi-step reaction with 2 steps
1: 1,2-dichloro-ethane / 3.25 h / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C
View Scheme
6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

glycine
56-40-6

glycine

7-chloro-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione
5973-28-4

7-chloro-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

Conditions
ConditionsYield
Stage #1: 6-chloro-N-methylisatoic anhydride; glycine With acetic acid at 130℃; for 7h;
Stage #2: With sodium hydroxide; water; sodium hydrogencarbonate pH=~ 9 - 10;
100%
With acetic acid at 130℃; for 7h;
With acetic acid at 130℃; for 7h;
6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

diethyl malonate
105-53-3

diethyl malonate

ethyl 6-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate
52851-65-7

ethyl 6-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl acetamide at 20 - 90℃; for 0.5h;
Stage #2: 6-chloro-N-methylisatoic anhydride In N,N-dimethyl acetamide at 20 - 110℃;
97%
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 6-chloro-N-methylisatoic anhydride In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere;
30%
4-(4-bromophenyl)-4-vinyl-1,3-dioxolan-2-one
1459246-69-5

4-(4-bromophenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(Z)-6-(4-bromophenyl)-11-chloro-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

(Z)-6-(4-bromophenyl)-11-chloro-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;93%
4-(4-bromophenyl)-4-vinyl-1,3-dioxolan-2-one
1459246-69-5

4-(4-bromophenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

C19H15BrClNO4

C19H15BrClNO4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;93%
4-phenyl-4-vinyl-1,3-dioxolan -2-one
1459246-62-8

4-phenyl-4-vinyl-1,3-dioxolan -2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(Z)-11-chloro-1-methyl-6-phenyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

(Z)-11-chloro-1-methyl-6-phenyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 4h;87%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 4h; Schlenk technique; Inert atmosphere;83%
4-(4-methylphenyl)-4-vinyl-1,3-dioxolan-2-one
1638152-34-7

4-(4-methylphenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(Z)-11-chloro-1-methyl-6-(p-tolyl)-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

(Z)-11-chloro-1-methyl-6-(p-tolyl)-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 8h;87%
4-phenyl-4-vinyl-1,3-dioxolan -2-one
1459246-62-8

4-phenyl-4-vinyl-1,3-dioxolan -2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

C19H16ClNO4

C19H16ClNO4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 4h;87%
N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

5-chloro-N-[2-(diethylamino)ethyl]-2-methylaminobenzamide
159619-29-1

5-chloro-N-[2-(diethylamino)ethyl]-2-methylaminobenzamide

Conditions
ConditionsYield
In 1,4-dioxane at 60℃; for 2h;85%
4-(4-chlorophenyl)-4-vinyl-1,3-dioxolan-2-one
1459246-68-4

4-(4-chlorophenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(Z)-11-chloro-6-(4-chlorophenyl)-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

(Z)-11-chloro-6-(4-chlorophenyl)-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;85%
4-(4-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one
1459246-67-3

4-(4-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(Z)-11-chloro-6-(4-methoxyphenyl)-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

(Z)-11-chloro-6-(4-methoxyphenyl)-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 6h;85%
4-(4-chlorophenyl)-4-vinyl-1,3-dioxolan-2-one
1459246-68-4

4-(4-chlorophenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

C19H15Cl2NO4

C19H15Cl2NO4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;85%
4-(4-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one
1459246-67-3

4-(4-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

C20H18ClNO5

C20H18ClNO5

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 6h;85%
phenylhydrazine
100-63-0

phenylhydrazine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(2-bromophenyl)-6-chloro-1-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one
1452386-56-9

2-(2-bromophenyl)-6-chloro-1-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
Stage #1: phenylhydrazine; 6-chloro-N-methylisatoic anhydride In acetonitrile Reflux;
Stage #2: ortho-bromobenzaldehyde With toluene-4-sulfonic acid In acetonitrile at 81℃;
84%
6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

glycine
56-40-6

glycine

A

5-chloro-2-(methylamino)hippuric acid
72952-53-5

5-chloro-2-(methylamino)hippuric acid

B

5-chloro-2-methylamino-benzoic acid
33280-14-7

5-chloro-2-methylamino-benzoic acid

Conditions
ConditionsYield
With sodium carbonate In waterA 83.9%
B 7%
6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

(Z)-6-chloro-1-methyl-3-phenyl-2-(phenylimino)-2,3-dihydroquinazolin-4(1H)-one

(Z)-6-chloro-1-methyl-3-phenyl-2-(phenylimino)-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; zinc In acetonitrile at 100℃; for 10h; Sealed tube; Inert atmosphere;83%
6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

diethylaminopropylamine
104-78-9

diethylaminopropylamine

5-chloro-N-[3-(diethylamino)propyl]-2-methylamino benzamide

5-chloro-N-[3-(diethylamino)propyl]-2-methylamino benzamide

Conditions
ConditionsYield
In 1,4-dioxane; ethyl acetate81%
In 1,4-dioxane at 60℃; for 5h;80%
1-(2-aminoethyl)pyrrolidine
7154-73-6

1-(2-aminoethyl)pyrrolidine

petroleum ether-isopropanol-ammonia

petroleum ether-isopropanol-ammonia

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

5-chloro-2-methylamino-N-[2-(1-pyrrolidinyl)ethyl] benzamide

5-chloro-2-methylamino-N-[2-(1-pyrrolidinyl)ethyl] benzamide

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; dichloromethane80%
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

3-benzyl-7-chloro-1-methyl-3,4-dihydro-1H-benzo[d][1,3]diazepine-5(2H)-one
1261594-23-3

3-benzyl-7-chloro-1-methyl-3,4-dihydro-1H-benzo[d][1,3]diazepine-5(2H)-one

Conditions
ConditionsYield
With lithium fluoride In acetonitrile at 35℃; for 3h; Inert atmosphere; Molecular sieve; Sonication;76%
1-(phenylmethyl)pyrrolidine-2,4-dione
30125-76-9

1-(phenylmethyl)pyrrolidine-2,4-dione

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

2-benzyl-7-chloro-4-methyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline-1,9(4H)-dione

2-benzyl-7-chloro-4-methyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline-1,9(4H)-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 2h; Sealed tube; Inert atmosphere; Molecular sieve;76%
4-(2-AMINOETHYL)MORPHOLINE
2038-03-1

4-(2-AMINOETHYL)MORPHOLINE

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

5-chloro-2-methylamino-N-<2-(4-morpholinyl)ethyl>-benzamide
92299-77-9

5-chloro-2-methylamino-N-<2-(4-morpholinyl)ethyl>-benzamide

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Ambient temperature;75%
ethanolamine
141-43-5

ethanolamine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

5-Chlor-N-(2-hydroxy-aethyl)-2-methylamino-benzamid
4927-76-8

5-Chlor-N-(2-hydroxy-aethyl)-2-methylamino-benzamid

Conditions
ConditionsYield
In 1,4-dioxane at 60℃; for 1.5h;74%
tryptamine
61-54-1

tryptamine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

3-chloro-14-methyl-8,13,13b,14-tetrahydro-7H-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5-one

3-chloro-14-methyl-8,13,13b,14-tetrahydro-7H-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5-one

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; trifluoroacetic anhydride In N,N-dimethyl acetamide at 100℃; for 5h;74%
dimethyl(prop-2-yn-1-yl)sulfonium bromide
23451-62-9

dimethyl(prop-2-yn-1-yl)sulfonium bromide

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

6-chloro-1,2-dimethyl-3-(methylthio)quinolin-4(1H)-one

6-chloro-1,2-dimethyl-3-(methylthio)quinolin-4(1H)-one

Conditions
ConditionsYield
With dmap In acetonitrile at 60℃; for 5h;70%
6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

4,9-dihydro-6-methoxy-3H-pyrido[3,4-b]indole
7212-59-1

4,9-dihydro-6-methoxy-3H-pyrido[3,4-b]indole

C20H18ClN3O2
1394329-48-6

C20H18ClN3O2

Conditions
ConditionsYield
In dichloromethane at 45℃; for 6h;69%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(S)-7-chloro-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

(S)-7-chloro-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Conditions
ConditionsYield
With acetic acid for 18h; Reflux;67%
With acetic acid for 16h; Reflux;67%
4-(4-(benzyloxy)phenyl)-4-vinyl-1,3-dioxolan-2-one

4-(4-(benzyloxy)phenyl)-4-vinyl-1,3-dioxolan-2-one

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(Z)-6-(4-(benzyloxy)phenyl)-11-chloro-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

(Z)-6-(4-(benzyloxy)phenyl)-11-chloro-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 3h;67%

14529-12-5Relevant articles and documents

Benzoxazepine-Derived Selective, Orally Bioavailable Inhibitor of Human Acidic Mammalian Chitinase

Andryianau, Gleb,Bartoszewicz, Agnieszka,Czestkowski, Wojciech,Dymek, Barbara,Dzwonek, Karolina,Golab, Jakub,Golebiowski, Adam,Gruza, Mariusz,Koralewski, Robert,Kowalski, Michal,Matyszewski, Krzysztof,Mazur, Marzena,Niedziejko, Piotr,Olczak, Jacek,Olejniczak, Sylwia,Piotrowicz, Michal C.,Pluta, Elzbieta,Rajkiewicz, Adam A.,Rymaszewska, Aleksandra,Salamon, Magdalena,Sklepkiewicz, Piotr L.,Stefaniak, Filip,Welzer, Mikolaj,Zagozdzon, Agnieszka

, p. 1228 - 1235 (2020/07/03)

Human acidic mammalian chitinase (hAMCase) is one of two true chitinases in humans, the function of which remains elusive. In addition to the defense against highly antigenic chitin and chitin-containing pathogens in the gastric and intestinal contents, AMCase has been implicated in asthma, allergic inflammation, and ocular pathologies. Potent and selective small-molecule inhibitors of this enzyme have not been identified to date. Here we describe structural modifications of compound OAT-177, a previously developed inhibitor of mouse AMCase, leading to OAT-1441, which displays high activity and selectivity toward hAMCase. Significantly reduced off-target activity toward the human ether-à-go-go-related gene (hERG) and a good pharmacokinetic profile make OAT-1441 a potential candidate for further preclinical development as well as a useful tool compound to study the physiological role of hAMCase.

Synthesis and antimicrobial activity of novel 4-Hydroxy-2-quinolone analogs

Khamkhenshorngphanuch, Thitiphong,Kulkraisri, Kittipat,Janjamratsaeng, Alongkorn,Plabutong, Napasawan,Thammahong, Arsa,Manadee, Kanitta,Na Pombejra, Sarisa,Khotavivattana, Tanatorn

, (2020/07/30)

Alkyl quinolone has been proven to be a privileged scaffold in the antimicrobial drug discovery pipeline. In this study, a series of new 4-hydroxy-2-quinolinone analogs containing a long alkyl side chain at C-3 and a broad range of substituents on the C-6 and C-7 positions were synthesized. The antibacterial and antifungal activities of these analogs against Staphylococcus aureus, Escherichia coli, and Aspergillus flavus were investigated. The structure-activity relationship study revealed that the length of the alkyl chain, as well as the type of substituent, has a dramatic impact on the antimicrobial activities. Particularly, the brominated analogs 3j with a nonyl side chain exhibited exceptional antifungal activities against A. flavus (half maximal inhibitory concentration (IC50) = 1.05 μg/mL), which surpassed that of the amphotericin B used as a positive control. The antibacterial activity against S. aureus, although not as potent, showed a similar trend to the antifungal activity. The data suggest that the 4-hydroxy-2-quinolone is a promising framework for the further development of new antimicrobial agents, especially for antifungal treatment.

Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones

Lee, Ansoo,Zhu, Joshua L.,Feoktistova, Taisiia,Brueckner, Alexander C.,Cheong, Paul H.-Y.,Scheidt, Karl A.

, p. 5941 - 5945 (2019/04/03)

A direct decarboxylative strategy for the generation of aza-o-quinone methides (aza-o-QMs) by N-heterocyclic carbene (NHC) catalysis has been discovered and explored. This process requires no stoichiometric additives in contrast with current approaches. Aza-o-QMs react with trifluoromethyl ketones through a formal [4+2] manifold to access highly enantioenriched dihydrobenzoxazin-4-one products, which can be converted to dihydroquinolones through an interesting stereoretentive aza-Petasis–Ferrier rearrangement sequence. Complementary dispersion-corrected density functional theory (DFT) studies provided an accurate prediction of the reaction enantioselectivity and lend further insight to the origins of stereocontrol. Additionally, a computed potential energy surface around the major transition structure suggests a concerted asynchronous mechanism for the formal annulation.

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