Ethanolamine ester

Antispasmodic activity, interestingly, is maintained even in the face of the deletion of the ethanolamine ester side chain. Reaction of anisaldehyde with potassium cyanide and dibutylamine hydrochloride affords the corresponding a-aminonitrile (72) (a functionality analogous to a cyanohydrin). Treatment with sulfuric acid hydrolyzes the nitrile to the amide to yield ambucet-amide (73). ... 

From another leguminous plant now classified in the Caesalpiniaceae, Erythrophleum chlorostachys, several alkaloids typified by norerythrostachamine (94) were isolated and their structures elucidated they occur as ethanolamine esters of diterpene acids, but readily rearrange to the corresponding amides [ 111J. These alkaloids are highly toxic and are responsible for cattle poisoning in the Darwin area. 

Ethanolamine ester, C(HI0NjOj, ethanolamine oxiniacate, NovacyL... 

Davies et al. synthesized H-T2-H 2 in 50% yield reacting the ethanolamine ester of di(2-thienyl)borinic acid with iV-bromosuccinimide (NBS) as brominating agent. The investigation aimed at the use of the easily isolable borinic acids as intermediates in synthetic organic chemistry [57]. 

They are conveniently isolated and stored as ethanolamine esters, which owe their air-stability to their cyclic boroxazolidine structure (3.24) in which the four co-ordinate boron is protected from attack by nucleophiles such as water or molecular oxygen. 8-Hydroxyquinoline, j8-ketoesters and jS-keto enols form similar derivatives, and their acetylacetonates (3.25) result from the smooth cleavage of one alkyl group from trialkylboranes R3B ... 

A new promising method for the synthesis of mixed biaryls consists in the reaction of the ethanolamine esters of diarylboronic acids with NBS in dichloro-methane/aqueous buffer at pH 9. In this way, 2- and 3-phenylthiophen, 2,2 -bi-thienyl, and 2-(2-thienyl)furan were obtained. The nitration of 2,3 -bithienyl has been studied. 2-Nitro-2 -amino-3,3 -bithienyl and 3-nitro-3 -amino-2,2 -bithienyl have been found to be stable. Carbonyl derivatives of 2-aryl-thiophens have been prepared, and reactivity constants for 2-aryl-thiophens determined. Some 2,5-bis(4 -n-alkyldiphenyl-4"-yl)thiophens, which are liquid crystals, have been prepared from the corresponding 1,4-diketones and P4S10. Various naphthyl-thiophens have been synthesized in order to study their anti-inflammatory and antibacterial properties. ... 

Due to the convenience of the Wenker aziridine formation from P-aminoethyl sulfate ester (4) and base, many improvements ensued. Leighton et al. improved the yield of the first step for the formation of sulfate ester 4. First of all, both ethanolamine and 95% sulfuric acid were diluted with half of their weight of water and then slowly mixed together at 0 C. Finally, by keeping the temperature below 145 C, sulfate ester 4 was obtained in 90-95% yield. 

ESTERS OF AMINOBENZOIC ACIDS AND ALKANOLAMINES a. Derivatives of Ethanolamine... 

The simplification of the local anesthetic phaimacophore of cocaine to an aryl substituted ester of ethanolamine has been described previously. Atropine (S2) is a structurally closely related natural product whose main biologic action depends on inhibition of the parasympathetic nervous system. Among its many other actions, the compound exerts useful spasmolytic effects. 

It was therefore of some interest to so modify the molecule as to maximize this particular activity at the expense of the side effects. In much the same vein as the work on cocaine, the structural requirements for the desired activity had at one time been whittled down to embrace in essence an a-substituted phenylacetic acid ester of ethanolamine (S3). 

Porous glass (PG) modified with covalently adsorbed poly(p-nitrophenyl acrylate), as described in Sect. 4.1, turned out to be a highly suitable carrier for immobilization of various biospecific ligands and enzymes. When the residual active ester groups of the carrier were blocked by ethanolamine, the immobilized ligands when bound to the solid support via hydrophilic and flexible poly(2-hydroxyethyl acrylamide). The effective biospecific binding provided by the ligands... 

These compounds constimte as much as 10% of the phospholipids of brain and muscle. StmcmraUy, the plasmalogens resemble phosphatidylethanolamine but possess an ether link on the sn- carbon instead of the ester link found in acylglycerols. Typically, the alkyl radical is an unsamrated alcohol (Figure 14-10). In some instances, choline, serine, or inositol may be sub-stimted for ethanolamine. 

PGIP, purified fi om P.vulgaris hypocotyls [11], was immobilized to the sensor ch via amine coupling. A continuous flow of HBS buffer (5 pl/min) was mantained over the sensor surface. The carboxylated dextran matrix of the sensor surface was first activated by a 6-min injection of a mixture of N-hydroxy-succinimide and N-ethyl-N - (3-diethylaminopropyl) carbodiimide, followed by a 7-min injection of PGIP (lOng/pl in 10 mM acetate, pH 5.0). Hie immobilization procedure was con leted by a 7-min injection of 1 M ethanolamine hydrochloride to block the remaining ester groups. 

High boiling polar compounds, diols, phenols, methyl esters of. dicarboxylic acids, amines, diamines, ethanolamines, amides, aldehydes and ketones. 

Allylic boranes such as 9-allyl-9-BBN react with aldehydes and ketones to give allylic carbinols. The reaction begins by Lewis acid-base coordination at the carbonyl oxygen, which both increases the electrophilicity of the carbonyl group and weakens the C-B bond to the allyl group. The dipolar adduct then reacts through a cyclic TS. Bond formation takes place at the 7-carbon of the allyl group and the double bond shifts.36 After the reaction is complete, the carbinol product is liberated from the borinate ester by displacement with ethanolamine. Yields for a series of aldehydes and ketones were usually above 90% for 9-allyl-9-BBN. 

In analogous fashion, ester interchange between methyl benzilate and N-ethyl-N-n-propyl-ethanolamine yields benapryzine (63). 5... 

Synthesis of 1-boraadamantane adducts with ethanolamine, L-phenylalanine, L-cysteine and and L-leucine methyl esters was reported (Table 3). The structures of three of them were supported by X-ray analysis (Table 1) <2003JME2823>. 

Phospholipids are also found which have similar structures (Table 12.6). These include lysophospholipids, which have only one of the two possible positions of glycerol esterified, almost invariably at carbon 1, and the plas-malogens, in which there is a long chain vinyl ether at carbon 1 instead of a fatty acid ester. These compounds also contain an amino alcohol, which may be either serine, ethanolamine or choline. Other rarer phospholipids are the monoacyl monoether, the diether and the phosphono forms. 

Figure 12.12 Sphingomyelins. Sphingomyelins are esters of a ceramide and phospho-ryl choline. However, similar compounds are ceramide-1-phosphoryl ethanolamines and phosphono forms of sphingolipids. Ceramides W-acyl-sphingosines) are amides of a long chain di- or trihydroxy base containing 12 to 22 carbon atoms, of which sphingosine (4-sphingenine) is the commonest, and a long chain fatty acid whose acyl chain is shown by R1. This may contain up to 26 carbon atoms.

Ethyl p-nitrophenyl benzenethionophosphate, see EPN Ethyl p-nitrophenyl benzenethiophosphonate, see EPN Ethyl p-nitrophenyl ester, see EPN Ethyl p-nitrophenyl phenylphosphonothioate, see EPN O-Ethyl O-4-nitrophenyl phenylphosphonothioate, see EPN O-Ethyl O-p-nitrophenyl phenylphosphonothioate, see EPN Ethyl p-nitrophenyl thionobenzenephosphate, see EPN Ethyl p-nitrophenyl thionobenzenephosphonate, see EPN Ethylolamine, see Ethanolamine Ethyl oxide, see Ethyl ether Ethyl parathion, see Parathion Ethylpentamethylene, see Ethylcyclopentane 2-Ethylpentane, see 3-Methylhextane O-Ethyl phenyl / nitrophenyl phenylphosphorothioate, see EPN... 

The simplest of the glycerophospholipids is phosphatidic acid, in which phosphate is linked to the third hydroxyl function, forming a phosphate ester. More complex glycerophospholipids are derivatives of phosphatidic acid in which one of several groups is attached commonly choline, ethanolamine, serine, or myo-inositol. Structures are collected in table 19.1. 

A compound with the same molecular weight as anandamide, but with a shorter retention time, was identified as O-arachidonoyl ethanolamine (arachidonic acid and ethanolamine joined by an ester linkage) (EC50 = 1906 nM). Based on this opposite orientation, the molecule was named virodhamine from the Sanskrit word, virodha, which means opposition. 

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