Nitrosation of Glycine Ethyl Ester and Ethyl Diazoacetate To Give the Alkylating Agent and Mutagen Ethyl Chloro(hydroximino)acetate

2004 ◽  
Vol 17 (3) ◽  
pp. 416-423 ◽  
Author(s):  
Lin Zhou ◽  
James Haorah ◽  
Sheng C. Chen ◽  
Xiaojie Wang ◽  
Carol Kolar ◽  
...  
Keyword(s):  
Ethyl Ester ◽  
Alkylating Agent ◽  
Ethyl Diazoacetate ◽  
Glycine Ethyl Ester

scholarly journals Some metabolites of 1-bromobutane in the rabbit and the rat

1968 ◽  
Vol 109 (5) ◽  
pp. 727-736 ◽  
Author(s):  
Sybil P. James ◽  
D. A. Jeffery ◽  
Rosemary H. Waring ◽  
P. B. Wood
Keyword(s):  
Lactic Acid ◽  
Ethyl Ester ◽  
Rat Liver ◽  
Hydroxy Acid ◽  
Rabbit Liver ◽  
Mercapturic Acid ◽  
Acid Form ◽  
Rat Urine ◽  
Glycine Ethyl Ester

1. Rabbits and rats dosed with 1-bromobutane excrete in urine, in addition to butylmercapturic acid, (2-hydroxybutyl)mercapturic acid, (3-hydroxybutyl)mercapturic acid and 3-(butylthio)lactic acid. 2. Although both species excrete both the hydroxybutylmercapturic acids, only traces of the 2-isomer are excreted by the rabbit. The 3-isomer has been isolated from rabbit urine as the dicyclohexylammonium salt. 3. 3-(Butylthio)lactic acid is formed more readily in the rabbit; only traces are excreted by the rat. 4. Traces of the sulphoxide of butylmercapturic acid have been found in rat urine but not in rabbit urine. 5. In the rabbit about 14% and in the rat about 22% of the dose of 1-bromobutane is excreted in the form of the hydroxymercapturic acids. 6. Slices of rat liver incubated with S-butylcysteine or butylmercapturic acid form both (2-hydroxybutyl)mercapturic acid and (3-hydroxybutyl)mercapturic acid, but only the 3-hydroxy acid is formed by slices of rabbit liver. 7. S-Butylglutathione, S-butylcysteinylglycine and S-butylcysteine are excreted in bile by rats dosed with 1-bromobutane. 8. Rabbits and rats dosed with 1,2-epoxybutane excrete (2-hydroxybutyl)mercapturic acid to the extent of about 4% and 11% of the dose respectively. 9. The following have been synthesized: N-acetyl-S-(2-hydroxybutyl)-l-cysteine [(2-hydroxybutyl)mercapturic acid] and N-acetyl-S-(3-hydroxybutyl)-l-cysteine [(3-hydroxybutyl)mercapturic acid] isolated as dicyclohexylammonium salts, N-toluene-p-sulphonyl-S-(2-hydroxybutyl)-l-cysteine, S-butylglutathione and N-acetyl-S-butylcysteinyl-glycine ethyl ester.

Iron-Catalyzed Cyclopropanation with Glycine Ethyl Ester Hydrochloride in Water

2012 ◽  
Vol 14 (8) ◽  
pp. 2162-2163 ◽  
Author(s):  
Bill Morandi ◽  
Amund Dolva ◽  
E. M. Carreira
Keyword(s):  
Ethyl Ester ◽  
Ester Hydrochloride ◽  
Glycine Ethyl Ester

Protection of Corn (Zea mays) from Acetanilide Herbicidal Injury with the Antidote R-25788

Weed Science ◽  
1978 ◽  
Vol 26 (6) ◽  
pp. 653-659 ◽  
Author(s):  
J. R. C. Leavitt ◽  
Donald Penner
Keyword(s):  
Zea Mays ◽  
Ethyl Ester ◽  
Isopropyl Ester ◽  
Weed Species ◽  
Greenhouse Study ◽  
Glycine Ethyl Ester

The antidote R-25788 (N,N-diallyl-2,2-dichloroacetamide) protected corn (Zea mays L. ‘DeKalb 315A’) seedlings from injury caused by the acetanilide herbicides, alachlor [2-chloro-2′,6′-diethyl-N-(methoxymethyl)acetanilide], metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide], H-22234 [N-chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester], and H-26910 [N-chloroacetyl-N-(2-methyl-6-ethylphenyl)glycine isopropyl ester] in a greenhouse study. R-25788, however, did not protect four weed species tested. R-25788 only partially protected corn from injury caused by acetochlor [2-chloro-N-(ethoxymethyl)-6′-ethyl-o-acetotoluidide]. R-25788 was an effective antidote whether applied preemergence, preplant-incorporated, or as a tank mix. Injury symptoms caused by EPTC (S-ethyl dipropylthiocarbamate) and the acetanilide herbicides were similar; both caused leaf twisting and rolling, and at high rates leaves failed to emerge through the coleoptile.

scholarly journals Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 4009
Author(s):  
István Köteles ◽  
Károly Mazák ◽  
Gergő Tóth ◽  
Boglárka Tűz ◽  
Sándor Hosztafi
Keyword(s):  
Ethyl Ester ◽  
Peptide Bond ◽  
Ethyl Acrylate ◽  
Alkaline Media ◽  
Carrier Protein ◽  
Amino Group ◽  
Carboxylic Group ◽  
Promising Alternative ◽  
Glycine Ethyl Ester ◽  
Work Up

Vaccination could be a promising alternative warfare against drug addiction and abuse. For this purpose, so-called haptens can be used. These molecules alone do not induce the activation of the immune system, this occurs only when they are attached to an immunogenic carrier protein. Hence obtaining a free amino or carboxylic group during the structural transformation is an important part of the synthesis. Namely, these groups can be used to form the requisite peptide bond between the hapten and the carrier protein. Focusing on this basic principle, six nor-morphine compounds were treated with ethyl acrylate and ethyl bromoacetate, while the prepared esters were hydrolyzed to obtain the N-carboxymethyl- and N-carboxyethyl-normorphine derivatives which are considered as potential haptens. The next step was the coupling phase with glycine ethyl ester, but the reactions did not work or the work-up process was not accomplishable. As an alternative route, the normorphine-compounds were N-alkylated with N-(chloroacetyl)glycine ethyl ester. These products were hydrolyzed in alkaline media and after the work-up process all of the derivatives contained the free carboxylic group of the glycine side chain. The acid-base properties of these molecules are characterized in detail. In the N-carboxyalkyl derivatives, the basicity of the amino and phenolate site is within an order of magnitude. In the glycine derivatives the basicity of the amino group is significantly decreased compared to the parent compounds (i.e., morphine, oxymorphone) because of the electron withdrawing amide group. The protonation state of the carboxylate group significantly influences the basicity of the amino group. All of the glycine ester and the glycine carboxylic acid derivatives are currently under biological tests.

scholarly journals Vaccines against Drug Abuse: Morphine-Hapten Design and Synthesis

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 48
Author(s):  
István Köteles ◽  
Sándor Hosztafi
Keyword(s):  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Structural Changes ◽  
Drugs Of Abuse ◽  
Covalent Bond ◽  
Ethyl Acrylate ◽  
Alkaline Media ◽  
Hapten Design ◽  
Glycine Ethyl Ester ◽  
Work Up

Drugs of abuse are small molecules that typically do not induce an antibody response following the administration. To induce antibodies against these kind of molecules, structural changes have to be made to obtain so called “haptens”. The hapten must be coupled to immunogenic proteins, called “carriers”. These connected derivatives are typically drug-linker adducts, in which the linker has a terminal functional group (i.e., carboxylic acid or aliphatic amine) that forms a covalent bond with the carrier. The efficacy of these conjugate vaccines depends on several factors including hapten design, coupling strategy, hapten density, carrier protein selection, and vaccine adjuvant. Six nor-normorphine compounds were reacted with ethyl acrylate and ethyl bromoacetate. After the synthesis of the specific esters we hydrolyzed them to receive the N-carboxymethyl- and N-carboxyethyl-normorphine derivatives. The next step was the coupling phase with glycine ethyl ester, but the reactions didn’t work or the work-up process was not accomplishable. As an alternative route the normorphine-compounds were reacted with N-chloroacetyl glycine ethyl ester. These products were hydrolyzed in alkaline media and after the work-up process all of the derivatives contained the free carboxylic group of the glycine sidechain. All of the glycine ester and the glycine carboxylic acid derivatives are under biological tests.

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