Synthesis of sulfide- and disulfide-type bisaporphines from thebaine
نویسندگان
چکیده
The rearrangement reaction of thebaine (1) with methanesulfonic acid, in the presence of hydrogen sulfide, resulted in a sulfide-type bisaporphine 13, instead of the expected thiol 12. The acidic hydrolysis of the thiocyanato derivatives 3, 9, 20 and 21, obtained from thebaine (1), as well as the reduction of 9 and 21 with sodium borohydride yielded disulfide-type bisaporphines 16 and 23.
منابع مشابه
Synthesis of Zinc Dimethyldithiocarbamate by Reductive Disulfide Bond Cleavage of Tetramethylthiuram Disulfide in Presence of Zn2+
The zinc(II) complex [Zn2(dmdtc)2(μ-dmdtc)2] has been synthesized directly from thiram ligand, containing a disulfide bond {dmdtc = N,N-dimethyldithiocarbamate; thiram = N,N-tetramethylthiuram disulfide}, and characterized by elemental analysis and spectroscopic methods. Surprisingly thiram, undergoes a reductive disulfide bond scission upon reaction with Zn2+ in methanolic media to give the [Z...
متن کاملSynthesis of linear and cyclic disulfide heptapeptides of Longicalycinin A and evaluation of toxicity on cancerous cells HepG2 and HT-29
In this work, linear and cyclic disulfide heptapeptides of Longicalycinin A have been successfully synthesized by solid phase methodology with Fmoc /t-Bu and solution phase, respectively. 2-Chlorotrityl chloride resin (2-CTC) was used as a solid support. The synthesized linear disulfide analogue of Longicalycinin A was cleaved from the resin as a protected peptide. The final deprotection was pe...
متن کاملMagnetic Resonance Spectroscopic Investigations of Poly(p-Phenylene Sulfide/Disulfide), PPS/DS
Recently a new process for the synthesis of the commercially important semi-crystalline, engineering thermoplastic poly(p-phenylene sulfide/disulfide), PPS/DS, was presented [1]. This process, based on the reaction of p-diiodobenzene (DIB) and sulfur at elevated temperatures (Figure 1), generates a polymeric material containing para-substituted aromatic groups connected by sulfide and disulfide...
متن کاملSynthesis of linear and cyclic disulfide heptapeptides of Longicalycinin A and evaluation of toxicity on cancerous cells HepG2 and HT-29
In this work, linear and cyclic disulfide heptapeptides of Longicalycinin A have been successfully synthesized by solid phase methodology with Fmoc /t-Bu and solution phase, respectively. 2-Chlorotrityl chloride resin (2-CTC) was used as a solid support. The synthesized linear disulfide analogue of Longicalycinin A was cleaved from the resin as a protected peptide. The final deprotection was pe...
متن کاملOptimization of Thebaine Production using Adventitious Roots of Papaver bracteatum Lindle. by Alteration of Aeration Volume and Temperature in Bioreactor
Background: Nowadays, the optimization of the culture conditions in bioreactors is considered as an approach to produce secondary metabolites such as thebaine. Thebaine is the dominant alkaloid in Iranian poppy that is used as a precursor for the synthesis of analgesic compounds. Objective: Optimization of culture conditions of Papaver bracteatum adventitious roots in bioreactor for the scale...
متن کامل