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36394-75-9 Usage

Uses

Frequently used chiral building block. Also used to resolve a bicyclic α-hydroxylactone and to prepare chiral phosphonates used in an enantiomeric excess assay of unprotected amino acids. Useful chiral derivatizing agent.

Purification Methods

It is moisture sensitive and is hydrolysed to the corresponding acid. Check the IR spectrum. If the OH band above 3000cm -1 is too large and broad then the mixture should be refluxed with pure acetyl chloride for 1hour, evaporated and distilled under reduced pressure. [Julia & Sans J Chromatographic Sci 17 651 1979, Dolittle & Heath J Org Chem 49 5041 1984, Beilstein 3 II 189.]

Check Digit Verification of cas no

The CAS Registry Mumber 36394-75-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,3,9 and 4 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 36394-75:
(7*3)+(6*6)+(5*3)+(4*9)+(3*4)+(2*7)+(1*5)=139
139 % 10 = 9
So 36394-75-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H7ClO3/c1-3(5(6)8)9-4(2)7/h3H,1-2H3/t3-/m0/s1

36394-75-9 Well-known Company Product Price

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  • Aldrich

  • (447056)  (S)-(−)-2-Acetoxypropionylchloride  97%

  • 36394-75-9

  • 447056-5G

  • 1,034.05CNY

  • Detail

36394-75-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-(-)-2-ACETOXYPROPIONYL CHLORIDE

1.2 Other means of identification

Product number -
Other names [(2S)-1-chloro-1-oxopropan-2-yl] acetate

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:36394-75-9 SDS

36394-75-9Synthetic route

(S)-2-acetoxypropionic acid
535-17-1, 3853-80-3, 18668-00-3, 6034-46-4

(S)-2-acetoxypropionic acid

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

Conditions
ConditionsYield
With thionyl chloride at 50℃; for 2h;93.7%
With thionyl chloride at 20℃; Chlorination;31%
With thionyl chloride
sodium L-lactate
867-56-1

sodium L-lactate

acetyl chloride
75-36-5

acetyl chloride

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

Conditions
ConditionsYield
With hydrogenchloride; thionyl chloride In diethyl ether64%
sodium L-lactate
867-56-1

sodium L-lactate

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

C7H10O5

C7H10O5

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 0.25 h / 20 - 40 °C
2: thionyl chloride / 1,2-dichloro-ethane / 7 h / 40 °C
View Scheme
oxalyl dichloride
79-37-8

oxalyl dichloride

L-Lactic acid
79-33-4

L-Lactic acid

acetyl chloride
75-36-5

acetyl chloride

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

Conditions
ConditionsYield
In dichloromethane
L-Lactic acid
79-33-4

L-Lactic acid

acetyl chloride
75-36-5

acetyl chloride

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

Conditions
ConditionsYield
Stage #1: L-Lactic acid; acetyl chloride at 20℃; Schlenk technique; Inert atmosphere;
Stage #2: With thionyl chloride In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere;
C22H21N7O
1220700-96-8

C22H21N7O

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

C27H27N7O4
1220700-97-9

C27H27N7O4

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
(3S,4R)-tert-butyl 3-((((R)-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)(tetrahydro-2H-pyran-4-yl)methyl)amino)methyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1-carboxylate

(3S,4R)-tert-butyl 3-((((R)-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)(tetrahydro-2H-pyran-4-yl)methyl)amino)methyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1-carboxylate

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(3S,4R)-tert-butyl 3-(((S)-2-acetoxy-N-((R)-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)(tetrahydro-2H-pyran-4-yl)methyl)propanamido)methyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1-carboxylate

(3S,4R)-tert-butyl 3-(((S)-2-acetoxy-N-((R)-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)(tetrahydro-2H-pyran-4-yl)methyl)propanamido)methyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1.5h;100%
ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate
61586-78-5

ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(1R,2S)-2-((S)-2-Acetoxy-propionyloxy)-cyclohexanecarboxylic acid ethyl ester

(1R,2S)-2-((S)-2-Acetoxy-propionyloxy)-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
With pyridine In diethyl ether at 4℃; for 20h; Acylation;99%
[5,6-bis-(trimethyl-silanyloxy)-1,2,3,4,5,6-hexahydro-inden-3a-yl]-methanol

[5,6-bis-(trimethyl-silanyloxy)-1,2,3,4,5,6-hexahydro-inden-3a-yl]-methanol

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

2-acetoxypropionic acid 5,6-bis(trimethyl-silanyloxy)-1,2,3,4,5,6-hexahydro-1H-inden-3a-yl methyl ester

2-acetoxypropionic acid 5,6-bis(trimethyl-silanyloxy)-1,2,3,4,5,6-hexahydro-1H-inden-3a-yl methyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃; for 0.416667h;99%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

6-amino-5-fluoroindolin-2-one
150544-01-7

6-amino-5-fluoroindolin-2-one

acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester
1082989-94-3

acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester

Conditions
ConditionsYield
With piperidine In tetrahydrofuran at -40 - 20℃;99%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

6-amino-5-fluoroindolin-2-one
150544-01-7

6-amino-5-fluoroindolin-2-one

(S)-acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester
945381-83-9

(S)-acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester

Conditions
ConditionsYield
With piperidine In tetrahydrofuran at -40 - 20℃;99%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

3-amino-4-hydroxytoluene
95-84-1

3-amino-4-hydroxytoluene

(2S)-1-(2-hydroxy-5-methylphenylamino)-1-oxopropan-2-yl acetate
941301-38-8

(2S)-1-(2-hydroxy-5-methylphenylamino)-1-oxopropan-2-yl acetate

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane; acetone at 10 - 20℃;97%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-3-fluoro-4-nitrophenylalanine methyl ester
160247-85-8

(S)-3-fluoro-4-nitrophenylalanine methyl ester

(S)-2-((S)-2-Acetoxy-propionylamino)-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester

(S)-2-((S)-2-Acetoxy-propionylamino)-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 1h; Ambient temperature;96%
With dmap; triethylamine In dichloromethane Ambient temperature; Yield given;
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(R)-(3-Allyloxy-phenyl)-amino-acetic acid methyl ester
185112-21-4

(R)-(3-Allyloxy-phenyl)-amino-acetic acid methyl ester

(R)-((S)-2-Acetoxy-propionylamino)-(3-allyloxy-phenyl)-acetic acid methyl ester

(R)-((S)-2-Acetoxy-propionylamino)-(3-allyloxy-phenyl)-acetic acid methyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃; for 1h;96%
2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

4-chloropentyl (S)-(-)-2-acetoxypropionate

4-chloropentyl (S)-(-)-2-acetoxypropionate

Conditions
ConditionsYield
With bismuth(III) chloride In dichloromethane at 20℃;96%
4-Chlorodeacetylcolchicine
1267986-38-8

4-Chlorodeacetylcolchicine

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-4-chloro-N-(2-acetoxypropionyl)deacetyl colchicine

(S)-4-chloro-N-(2-acetoxypropionyl)deacetyl colchicine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Cooling with ice; Inert atmosphere;95%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

5-amino-2,4,6-triiodoisophthalic acid dichloride
37441-29-5

5-amino-2,4,6-triiodoisophthalic acid dichloride

S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride
60166-91-8

S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 0 - 20℃; Inert atmosphere;92.3%
In N,N-dimethyl acetamide at 0 - 20℃; for 38h; Inert atmosphere;91.4%
Stage #1: (S)-2-acetoxypropanoyl chloride In N,N-dimethyl acetamide at -2 - 0℃; for 1h;
Stage #2: 5-amino-2,4,6-triiodoisophthalic acid dichloride; metanol at 12℃; for 6h;
Stage #3: With 2-ethoxy-ethanol more than 3 stages;
90%
Stage #1: (S)-2-acetoxypropanoyl chloride In N,N-dimethyl acetamide at -2 - 0℃; for 1h;
Stage #2: 5-amino-2,4,6-triiodoisophthalic acid dichloride; metanol In N,N-dimethyl acetamide at 12℃; for 6h;
Stage #3: With 2-ethoxy-ethanol more than 3 stages;
89%
With N,N-dimethylacetamide hydrochloride In ISOPROPYLAMIDE at 10 - 25℃;
(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-2-Acetoxy-N-<(S)-α-methylbenzyl>propionamide
90687-81-3

(S)-2-Acetoxy-N-<(S)-α-methylbenzyl>propionamide

Conditions
ConditionsYield
With pyridine In dichloromethane for 1h;92%
With pyridine In dichloromethane at 0℃; for 1h;86%
(S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide
1092113-64-8

(S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid-N'-(2S)-acetoxypropionyl hydrazide
1092113-72-8

(S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid-N'-(2S)-acetoxypropionyl hydrazide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 1h;92%
methyl 2-Amino-5-trifluoromethylbenzoate
117324-58-0

methyl 2-Amino-5-trifluoromethylbenzoate

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-methyl 2-(2-acetoxypropionylamino)-5-trifluoromethyl benzoate

(S)-methyl 2-(2-acetoxypropionylamino)-5-trifluoromethyl benzoate

Conditions
ConditionsYield
In diethyl ether at -10 - 20℃; for 3h;92%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

diethylamine
109-89-7

diethylamine

2-(S)-acetylpropionyl-N,N-diethyl amide
160512-36-7

2-(S)-acetylpropionyl-N,N-diethyl amide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 12h; Ambient temperature;91%
2-(1,1-dimethylethyl)-benzenamine
6310-21-0

2-(1,1-dimethylethyl)-benzenamine

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide
215593-41-2

(2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide

Conditions
ConditionsYield
With pyridine at 25℃; for 3h;91%
3-(diphenylphosphinoyl)-2-iodo-phenol
854937-67-0

3-(diphenylphosphinoyl)-2-iodo-phenol

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-2-Acetoxy-propionic acid 3-(diphenyl-phosphinoyl)-2-iodo-phenyl ester
854937-68-1

(S)-2-Acetoxy-propionic acid 3-(diphenyl-phosphinoyl)-2-iodo-phenyl ester

Conditions
ConditionsYield
With TEA In dichloromethane at 20℃; for 1h;91%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

12(R)-benzoyloxy-5(S)-hydroxy icosa-8(E,Z),10(E)-diene 6,14-diynoate de methyle
124629-71-6, 124629-73-8, 131937-95-6

12(R)-benzoyloxy-5(S)-hydroxy icosa-8(E,Z),10(E)-diene 6,14-diynoate de methyle

Benzoic acid (2E,4E)-(1R,8S)-8-((R)-2-acetoxy-propionyloxy)-11-methoxycarbonyl-1-oct-2-ynyl-undeca-2,4-dien-6-ynyl ester
140611-23-0, 140694-42-4

Benzoic acid (2E,4E)-(1R,8S)-8-((R)-2-acetoxy-propionyloxy)-11-methoxycarbonyl-1-oct-2-ynyl-undeca-2,4-dien-6-ynyl ester

Conditions
ConditionsYield
With pyridine In diethyl ether90%
DL-alanine ethyl ester hydrochloride
617-27-6

DL-alanine ethyl ester hydrochloride

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

N-[(S)-2-acetoxypropanoyl]alanine ethyl ester

N-[(S)-2-acetoxypropanoyl]alanine ethyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane for 1h;90%
5(R)-Isoxazol-3-yloxymethyl-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one
252328-98-6

5(R)-Isoxazol-3-yloxymethyl-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

5(R)-Isoxazol-3-yloxymethyl-3-(4-(1-(2(S)-acetoxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one

5(R)-Isoxazol-3-yloxymethyl-3-(4-(1-(2(S)-acetoxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one

Conditions
ConditionsYield
In methanol; dichloromethane90%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

(S)-methyl 2-(2-acetoxypropanamido)benzoate
145041-21-0

(S)-methyl 2-(2-acetoxypropanamido)benzoate

Conditions
ConditionsYield
In diethyl ether at -10 - 20℃; for 3h;89.9%
In diethyl ether Yield given;
In diethyl ether at 0℃; Inert atmosphere; Schlenk technique;
5-amino-2,4,6-triiodoisophthaloyl dichloride

5-amino-2,4,6-triiodoisophthaloyl dichloride

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

L-5-(2-acetoxypropionylamino)-2,4,6-triiodoisophthaloyl dichloride

L-5-(2-acetoxypropionylamino)-2,4,6-triiodoisophthaloyl dichloride

Conditions
ConditionsYield
water In ISOPROPYLAMIDE at -2 - 20℃; for 21 - 23h;89%
[Mo(hydridotris(pyrazolyl)borate)(CO)2(η3-C6H8OTBS)]
1239990-18-1, 180892-49-3

[Mo(hydridotris(pyrazolyl)borate)(CO)2(η3-C6H8OTBS)]

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

dicarbonyl[hydridotris(1-pyrazolyl)borate][(η-1,2,3)-1-((S)-2-acetoxypropionyloxy)-2-cyclohexen-1-yl]molybdenum

dicarbonyl[hydridotris(1-pyrazolyl)borate][(η-1,2,3)-1-((S)-2-acetoxypropionyloxy)-2-cyclohexen-1-yl]molybdenum

Conditions
ConditionsYield
With [(C4H9)4N][SiF2(C6H5)3] In dichloromethane addn. of tetrabutylammonium salt to CH2Cl2 soln. of molybdenum compd., stirring for 30 min at room temp., addn. of acetoxypropionyl chloride, stirring at room temp. for 10 min; concg., flash chromy. (silica gel, hexanes/ethyl acetate (4:1)), recrystn. (CH2Cl2/hexanes), NMR and MS;89%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

L-tryptophan methyl ester
4299-70-1

L-tryptophan methyl ester

N-(O-acetoxypropionyl)-L-tryptophan methyl ester

N-(O-acetoxypropionyl)-L-tryptophan methyl ester

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane88.6%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-2-Acetoxypropanamide
50911-24-5

(S)-2-Acetoxypropanamide

Conditions
ConditionsYield
With ammonia In dichloromethane at 20℃; for 1h;88%
With dichloromethane; ammonia
Yield given;
(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-2-Acetoxy-N-<(R)-α-methylbenzyl>propionamide
90687-80-2

(S)-2-Acetoxy-N-<(R)-α-methylbenzyl>propionamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 1h;88%
With pyridine In dichloromethane for 1h;82%
(S)-2-acetoxypropanoyl chloride
36394-75-9

(S)-2-acetoxypropanoyl chloride

(S)-3-Amino-2-(1-tert-butyldimethylsilyloxy-2-methylpropyl)quinazolin-4(3H)-one
262600-86-2

(S)-3-Amino-2-(1-tert-butyldimethylsilyloxy-2-methylpropyl)quinazolin-4(3H)-one

3-(S)-2-Acetoxypropanoylamino-2-[(S)-1-tert-butyldimethylsilyloxy-2-methylpropyl]quinazolin-4(3H)-one
329729-36-4

3-(S)-2-Acetoxypropanoylamino-2-[(S)-1-tert-butyldimethylsilyloxy-2-methylpropyl]quinazolin-4(3H)-one

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 24h;88%

36394-75-9Relevant articles and documents

Synthesis, pharmacological evaluation and molecular docking of novel R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid as dual anti-inflammatory anti-platelet aggregation agents

Rong, Rong,Zhang, Rui-zhen,Wang, Xin,Dan, Yu-han,Zhao, Yun-li,Yu, Zhi-guo

, p. 967 - 978 (2019/12/12)

R-/S-2-(2-hydroxypropanamido) benzoic acid (R-/S-HPABA), marine-derived anti-inflammatory antiplatelet drugs, were initially synthesised in our group. However, preliminary research showed that R-/S-HPABA were eliminated rapidly because of extensive hydroxylation metabolism of phenyl ring in vivo. In order to reduce significant hydroxylation metabolism to improve pharmacological activity and bioavailability, trifluoromethyl group was incorporated into R-/S-HPABA to synthesise R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid (R-/S-HFBA), respectively. The purposes of this study were to report the synthesis of R-/S-HFBA and compare the anti-inflammatory antiplatelet effect and pharmacokinetic properties of R-/S-HFBA with those of R-/S-HPABA. Carrageenan-induced rat paw edema assay was used for the evaluation of the anti-inflammatory activity. R-/S-HFBA showed better results in inhibiting edema and were able to prolong the anti-inflammatory effect after carrageenan injection. The antiplatelet aggregation activity of R-/S-HFBA and R-/S-HPABA was studied on arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. The aggregation inhibition rate of R-/S-HFBA was significantly (p max, larger AUC0-∞, and longer t1/2, which, as expected, are more metabolically stable.

Preparation method and application of 2-lactoyl aminobenzoic acid

-

Paragraph 0039; 0040, (2017/08/30)

The invention relates to a new medicinal application of a chiral compound. The chiral compound is chemically named as R-/S-2-lactoyl aminobenzoic acid and has a structural formula as follows: formula (shown in the description). The compound is initially extracted and separated from secondary metabolite of microorganisms and can be obtained by virtue of a chemical synthetic method. An initial pharmacology experiment shows that the compound has good pain-easing and anti-inflammation activities and relatively low stimulation to gastrointestinal tracts. Recent researches prove that the compound has relatively good anti-platelet aggregation and anti-thrombus activities and is expected to be a novel non-steroidal anti-platelet aggregation and anti-thrombus drug.

3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes

Karabuga, Semistan,Karakaya, Idris,Ulukanli, Sabri

, p. 851 - 855 (2014/06/23)

A series of readily known enantiomerically pure 3-aminoquinazolinones 1a-d were synthesised from easily accessible chiral pool α-hydroxy acids and α-amino acids in only four steps without any requirement of chromatography. These quinazolinones were examined as chiral ligands for catalytic enantioselective diethylzinc and phenylacetylene additions to aldehydes. For enantioselective alkylations, the effects of temperature, solvent, diethylzinc and ligand criteria were analysed, and the desired chiral alcohols were obtained in up to 86% ee. 3-Aminoquinazolinones 1a-d were also shown to be very useful ligands in enantioselective alkynylations of aldehydes. Based upon the optimised conditions, the corresponding propargylic alcohols were obtained in up to 94% ee.

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