PREPARATION AND TOXICITY OF SOME ALKYL THIOPYROPHOSPHATES

1956 ◽  
Vol 34 (12) ◽  
pp. 1819-1832 ◽  
Author(s):  
R. A. McIvor ◽  
G. D. McCarthy ◽  
G. A. Grant
Keyword(s):  
High Yield ◽  
Inorganic Salts ◽  
Infrared Study ◽  
Toxicological Studies ◽  
Related Compounds

Several methods have been investigated for the synthesis of tetraalkyl thiopyrophosphates, including one that can be carried out very rapidly with high yield. Purification of these compounds proved exceedingly difficult, because they were sensitive to traces of acids or bases, and probably to inorganic salts at temperatures above 70 °C. All methods investigated yield only the thiono isomer, there being no evidence for the corresponding P—S—P isomer. Toxicological studies do not support the results reported by Fiszer and workers. None of the compounds is more toxic intravenously than tetraethyl pyrophosphate. The synthesis of several other related compounds for infrared study is reported.

The Pyrolytic Rearrangement of 1-Alkynoyl-3-methylpyrazoles: Synthesis of Pyrazolo[1,5-a]pyridin-5-ols and Related Compounds

1994 ◽  
Vol 47 (6) ◽  
pp. 991 ◽  
Author(s):  
RFC Brown ◽  
FW Eastwood ◽  
GD Fallon ◽  
SC Lee ◽  
RP Mcgeary
Keyword(s):  
Carbon Chain ◽  
Ring Structure ◽  
High Yield ◽  
Methyl Group ◽  
X Ray ◽  
X Ray Crystallography ◽  
Flash Vacuum Pyrolysis ◽  
Vacuum Pyrolysis ◽  
Fused Ring ◽  
Related Compounds

Flash vacuum pyrolysis of 1-(alkyn-2′-oyl)-3-methylpyrazoles at 650°/0.03 mm forms pyrazolo[1,5-a]pyridin-5-ols, often in high yield, which may bear substituents at C2, C3 or C7. In the absence of a 3-methyl group in the precursor, N-ethynylpyrazoles are formed in low yield. The formation of both types of product is interpreted as involving 3-(N-pyrazolyl)propadienones formed by N1 → N2 migration of the N-alkynoyl group with inversion of the three-carbon chain. The fused-ring structure of 2-methylpyrazolo[1,5-a]pyridin-5-ol (25) was established by X-ray crystallography of the O-benzoyl derivative (27).

scholarly journals Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase

1973 ◽  
Vol 51 (19) ◽  
pp. 3161-3169 ◽  
Author(s):  
Morris J. Robins ◽  
Gerald L. Basom
Keyword(s):  
Adenosine Deaminase ◽  
Methylene Chloride ◽  
Potassium Fluoride ◽  
Direct Conversion ◽  
Chloride Complex ◽  
High Yield ◽  
Mass Spectral ◽  
Quaternary Ammonium Chloride ◽  
Related Compounds

Trifluoroacetylation of 2′-deoxyinosine (2), obtained by enzymatic deamination of 2′-deoxyadenosine (1), gave the 3′,5′-bis-O-trifluoroacetate (3). Reaction of the electronegatively substituted deoxynucleoside, 3, with DMF-thionyl chloride complex in refluxing methylene chloride gave a high yield of 6-chloropurine 2′-deoxyriboside (4) after deblocking.Displacement of chloride of 4 by hydrosulfide to give 6-mercaptopurine 2′-deoxyriboside (5) followed by sulfur alkylation with p-nitrobenzyl bromide gave 6-S-(p-nitrobenzyl) thiopurine 2′-deoxyriboside (6) which was alternatively prepared by displacement of chloride from 4 by p-nitrobenzyl mercaptide, generated in situ from the isothiouronium salt. Methyl mercaptide reaction with 4 gave 6-methylthiopurine 2′-deoxyriboside (7). Treatment of 4 with trimethylamine gave the corresponding quaternary ammonium chloride (8) which was allowed to react with potassium fluoride to give 6-fluoropurine 2′-deoxyriboside (9). Respective amine displacements on 4 gave 6-benzylaminopurine 2'-deoxyriboside (10), and 6-hydroxylaminopurine 2′-deoxyriboside (11). Reaction of 4 with liquid ammonia completed the first reported transformation of 2′-deoxyinosine (2) to 2′-deoxyadenosine (1).Biological rationale for the synthesis of these 2′-deoxynucleosides and their evaluation as substrates of adenosine deaminase are discussed. Major mass spectral fragmentations are tabulated.

β-Carboline-3-carboxylic Acid (9H-Pyrido[3,4-b]indole-3-carboxylic Acid) and Related Compounds

1989 ◽  
Vol 42 (6) ◽  
pp. 813 ◽  
Author(s):  
JA Maclaren
Keyword(s):  
Carboxylic Acid ◽  
Rat Brain ◽  
High Yield ◽  
Brain Membranes ◽  
Novel Synthesis ◽  
Rat Brain Membranes ◽  
Related Compounds ◽  
Relative Inhibition

The synthesis of β-carboline-3-carboxylic acid and its esters (4) by oxidation of the corresponding 1,2,3,4-tetrahydro derivatives (2) or of the 3,4-dihydro derivatives (3) has been studied. A novel synthesis of the esters (3) [and hence of (4)] has been achieved in high yield by cyclization and elimination from the enamine (5). The relative inhibition of binding of a benzodiazepine to rat brain membranes by the esters (2)-(4) has been determined.

Beiträge zur Chemie des Phosphors, 621 Zur Frage des 31P-kernresonanzspektroskopischen Nachweises von monomerem und dimerem Phenylphosphor und der Ringgröße von Organyl-cyclophosphanen.

1976 ◽  
Vol 31 (5) ◽  
pp. 558-564 ◽  
Author(s):  
Marianne Baudler ◽  
Burkhard Carlsohn ◽  
Wolfgang Böhm ◽  
Goswin Reuschenbach
Keyword(s):  
Spectroscopic Investigation ◽  
Chemical Shifts ◽  
High Yield ◽  
Ring Size ◽  
Nmr Spectrum ◽  
Spectroscopic Evidence ◽  
Nmr Parameters ◽  
Similar Chemical ◽  
First Time ◽  
Related Compounds

The weak resonances at + 22 and + 49 ppm appearing in the 31P NMR spectrum of melts or solutions of (PPh)5 that have been attributed previously in the literature to “dimeric” and “monomeric phenylphosphorus” are caused by (PPh)6 and (PPh)4, respectively. This was proved by comparison with the 31P NMR parameters of related compounds and by 31P NMR spectroscopic investigation of authentic samples of (PPh)6 and (PPh)4, the latter of which was prepared in high yield from (Me3Si)PhP–PPh–PPh(SiMe3) and PhPCl2. (PEt)4 and mixed-substituted phenyl-ethyl-cyclotetraphosphanes exhibit similar chemical shifts as (PPh)4, corresponding mixed-substituted cyclohexaphosphanes have similar chemical shifts as (PPh)6. Generally, cyclophosphanes establish an equilibrium between (PR)n-species of different ring-size. Probably, the ring-interconversion proceeds via a multi-center mechanism. No 31P NMR spectroscopic evidence for the existence of free PPh or P2Ph2 under the conditions described could be detected. On thermolysis of (PEt)4 the existence of (PEt)3 was proved for the first time.

Nucleic acid related compounds. 38. Smooth and high-yield iodination and chlorination at C-5 of uracil bases and p-toluyl-protected nucleosides

1982 ◽  
Vol 60 (5) ◽  
pp. 554-557 ◽  
Author(s):  
Morris J. Robins ◽  
Philip J. Barr ◽  
Jerzy Giziewicz
Keyword(s):  
Nucleic Acid ◽  
Organic Solvents ◽  
High Yield ◽  
Iodine Monochloride ◽  
High Yields ◽  
Related Compounds

Treatment of uracil bases and protected nucleosides with iodine monochloride (ICl) gave the corresponding 5-iodouracil products in over 95% purified yields. Analogously facile chlorination was effected with iodobenzene dichloride (PhICl2). Protection of the nucleosides as p-toluyl esters provided reactants that were soluble in organic solvents and crystallized readily in high yields.

Chlordimeform and Related Compounds: Toxicological Studies with House Flies12

1973 ◽  
Vol 66 (1) ◽  
pp. 75-79 ◽  
Author(s):  
Charles O. Knowles ◽  
Surendra P. Shrivastava
Keyword(s):  
Toxicological Studies ◽  
Related Compounds
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