13947-20-1Relevant articles and documents
Mixed ligand palladium(II) complexes of N-hydroxy-methylsaccharin (Sac-CH2OH): Synthesis, characterization and biological studies
Al-Jibori, Subhi A.,Al-Janabi, Ahmed S.,Basak-Modi, Sucharita,Mohamed, Samar S.,Schmidt, Harry
, p. 917 - 921 (2015)
Reaction of Na2PdCl4 with two equivalents of N-hydroxymethylsaccharin (Sac-CH2OH) in the presence of NEt3 afforded trans-[Pd(κ2-Sac-CH2O)2]. Further reaction of [Pd(κ2-Sac-CH2O)2] with one equivalent of diphosphine (L2), Ph2P(CH2) n PPh2, (n = 1, dppm; 2, dppe and 3, dppp), Ph2P(S)(CH2)P(S)Ph2 (dppmS2) or Ph2P(O)(CH2)2P(O)Ph2 (dppeO2) afforded mixed ligand complexes [Pd(κ1-Sac-CH2O)2(L2)], while reaction with two equivalents of Ph3P, Ph3PO or Ph3PS (L) gave trans-[Pd(κ1-Sac-CH2O)2(L)2]. The N-hydroxymethylsaccharinate anion acts as a monodentate ligand, coordinating to the palladium center through the hydroxymethyl oxygen atom. The complexes were characterized by physico-chemical and spectroscopic methods. In addition, the free ligand N-hydroxymethylsaccharin and some of the complexes were screened in vitro for antibacterial activity.
A prodrug approach to increasing the oral potency of a phenolic drug. 1. Synthesis, characterization, and stability of an O-(imidomethyl) derivative of 17β-estradiol
Patel,Prankerd,Sloan
, p. 1477 - 1481 (1994)
An O-(saccharinylmethyl) prodrug was synthesized to improve the poor oral potency of the phenolic drug 17β-estradiol. This O-(imidomethyl) type of prodrug was designed to undergo chemical hydrolysis and to be a poor substrate for enzymatic hydrolysis. At 37 °C, it was found to exhibit half- lives of about 13 min in 50% methanol:pH 7.0 (v/v) phosphate buffer, about 3 min in rat plasma, about 15 min in human plasma, and about 50 min in 20% rat liver homogenate. Introduction of the enzyme poison tetraethyl pyrophosphate or the protein denaturant sodium fluoride into rat plasma had no significant effect on the half-life. Thus, the observed increased rate of hydrolysis in biological media is not due to enzymatic catalysis but to a nonspecific solventlike effect. The fact that the rate of hydrolysis in the methanol:buffer exhibited a first-order dependence on the hydroxide ion concentration and that the rate of hydrolysis increased with increasing methanol concentrations up to 70% supported an S(N)2 mechanism of hydrolysis for the prodrug. These results suggest that an O-(imidomethyl) type prodrug is insensitive to enzymatic catalysis of hydrolysis yet may hydrolyze quickly enough to release 17β-estradiol faster than 17β-estradiol is conjugated and excreted.
Facile one-pot synthesis of 4-hydroxy-2-methyl-(2H)-1,2-benzothiazine-3- sulfonic acid 1,1-dioxide
Siddiqui, Waseeq A.,Ahmad, Saeed,Khan, Islam Ullah,Siddiqui, Hamid Latif,Weaver, George W.
, p. 767 - 773 (2007/10/03)
We report a convenient synthesis of 4-hydroxy-2-methyl-(2H)-1,2- benzothiazine-3-sulfonic acid-1,1-dioxide (6a) prepared in a novel one-pot reaction. The synthesis involves two transformations starting from 2-methyl-2H-1,2-benzothiazin-4-(3H)-one 1,1-dioxide (7) with an overall yield better than that from the stepwise process, as well as the alternate procedure starting from saccharin (1). One-pot synthesis of an important intermediate, saccharin-N-methane sulfonic acid (4), is also described. Copyright Taylor & Francis Group, LLC.
