Drug Latentiation

Kupchan, S. Morris; Casy, A. F.; Swintosky, Joseph V.

doi:10.1002/jps.2600540404

Cited by 24 publications

(5 citation statements)

References 30 publications

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“…2-Methyl-4-p-nitrophenyl-5-dichloroacetamido-l,3-dioxane (2). In a dry stoppered conical flask, paraldehyde (20 ml) was saturated with dry HC1.…”

Section: Methodsmentioning

confidence: 99%

“…2-Methyl-4-p-nitrophenyl-5-dichloroacetamido-l ,3-dioxane (2) was hydrolyzed very slowly indicating that acetals of this type are not suitable as latentiation forms. Maximum blood levels were observed 2 hr after oral administration of 3 in an anesthetized rat and then declined slowly. The mean blood levels of 1 and 3 at 2 hr after oral administration of equal doses (100 mg/kg) in rats were 12.75 (±1.31) and 2.48 (±0.31) pg/ml, respectively.…”

mentioning

confidence: 94%

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Acid-labile derivatives of chloramphenicol as potential latentiation forms

Gillet¹,

Abdel-Monem²

1973

J. Med. Chem.

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“…2-Methyl-4-p-nitrophenyl-5-dichloroacetamido-l,3-dioxane (2). In a dry stoppered conical flask, paraldehyde (20 ml) was saturated with dry HC1.…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 94%

Acid-labile derivatives of chloramphenicol as potential latentiation forms

Gillet¹,

Abdel-Monem²

1973

J. Med. Chem.

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“…Consequently, a plethora of chemical protocols have been explored to provide routes toward process improvements of an esterified variants of testosterone. Amongst the most common methods are those which employ activated carboxylic acid derivatives such as acid anhydrides or acid chlorides in the presence of basic amines such as triethylamine (Et 3 N), 40,41 pyridine (Py), [42][43][44][45][46][47][48][49] 4-(dimethylamino)pyridine (DMAP) 50 and/or N,Ndimethylaniline (DMA) 51 as well as a binary mixture of those amines (Py/DMAP), [52][53][54][55][56][57] respectively. A similar kind of conversions have been reported by Yadav et al 58 using potassium fluoride on alumina (KF-Al 2 O 3 ) as a solid base catalyst.…”

Section: Introductionmentioning

confidence: 99%

Highly efficient, solvent-free esterification of testosterone promoted by a recyclable polymer-supported tosylic acid catalyst under microwave irradiation

Borowiecki¹,

Kraszewski²

2019

Arkivoc

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“…Compound 1 was prepared by reaction of cholesterol and chloromethyl methyl ether in the presence of sodium hydride (1) and shown to be identical in all resDects with the anodic oxidation product. Reaction of 5a-cholestan-3P-01 under the same conditions however gave a mixture of 3P,3'P-(rnethylenedioxy)-5a-~holestane (2) and 3P-(methoxymethoxy)-5a-cholestane (3) in poor yield.…”

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confidence: 99%

Steroidal Acetals of Formaldehyde

Herz¹,

Lucero²,

Santoyo³

et al. 1971

Can. J. Chem.

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The anodic oxidation of cholesterol yields 30,3'P-(methy1enedioxy)-dicholest-5-ene. A new method for the preparation of methoxymethyl ethers of steroids is described. The n.m.r. and mass spectra of these compounds is reported.L'oxydation anodique du cholesterol conduit au (methyltnedioxy)-3B,3'P dicholestene-5. On decrit une nouvelle methode pour la preparation des ethers methoxymtthyles des steroides. On rapporte les spectres de r.m.n. et de masse de ces composes.Canadian Journal of Chemistry, 49, 2418 (1971) In order to confirm the identity of the main anodic oxidation product of choiesterol in aqueous acidic methanol as 3P,3'P-(methylenedioxy)-dicholest-5-ene (1) direct comparison with an authentic specimen was necessary.Compound 1 was prepared by reaction of cholesterol and chloromethyl methyl ether in the presence of sodium hydride (1) and shown to be identical in all resDects with the anodic oxidation product. Reaction of 5a-cholestan-3P-01 under the same conditions however gave a mixture of 3P,3'P-(rnethylenedioxy)-5a-~holestane (2) and 3P-(methoxymethoxy)-5a-cholestane (3) in poor yield.As an alternative method for preparing compound 1, the reaction of cholesterol and dimethoxymethane in the presence of acidic catalysts was investigated. The product thus obtained was 3P-(methoxymethoxy)-cholest-5-ene (4), the structure of which was confirmed by its n.m.r. (Table 1) and mass spectra (see below). This method was also used to prepare compound 3 and seems of general applicability. Methoxymethyl ethers have also been prepared by Kupchan et al. (I) by a modification of the method employing chloromethyl methyl ether.The mass spectrum of compound 1 differs from that of cholesterol only in the greater abundance of the ions mle 368 and 353 relative to 386 (the molecular ion of cholesterol). Higher mass ions cannot be detected and no metastable transition can be found in the first field-free region of the spectrometer (2) for the decomposition of the parent molecular ion ( M + , mle 784) to either 386 or 368. Evidently a very ready fragmentation, either thermal or electron impact induced, results in the formation of the molecular ions of cholesterol and cholestadiene. The mass spectrum of 3P-(methoxymethoxy)-cholest-5-ene (4) is also very similar to that of cholesterol and shows no parent molecular ion (mle 430). Higher mass ions are very weak in the spectrum of compound 2 but the decomposition 788 ( M + ) -t 402 can be detected in the first field-free region. The latter together with a fairly intense ion at mle 386 suggests a fragmentation producing (nominally) the molecular ion of methoxycholestane and of cholestanone. The mass spectrum of 3P-(methoxymethoxy)-5a-cholestane is remarkable. The molecular ion (mle 432) is one of the strongest in the spectrum while another (370) is derived from it by loss of methoxymethanol. Such an intense molecular ion appears to be 'Revision received March 30, 1971. without precedent for an acetal(3).' ' Can. J. Chem. Downloaded from www.nrcresearchpress.com by 54.201.150.21 ...

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Drug Latentiation

Cited by 24 publications

References 30 publications

Acid-labile derivatives of chloramphenicol as potential latentiation forms

Acid-labile derivatives of chloramphenicol as potential latentiation forms

Highly efficient, solvent-free esterification of testosterone promoted by a recyclable polymer-supported tosylic acid catalyst under microwave irradiation

Steroidal Acetals of Formaldehyde

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