32478-65-2Relevant articles and documents
Electrochemical anion pool synthesis of amides with concurrent benzyl ester synthesis
Mevan Dissanayake,Melville, Alex D.,Vannucci, Aaron K.
supporting information, p. 3165 - 3171 (2019/06/18)
An electrosynthesis method for amide bond formation has been developed in an attempt to increase the atom economy for this class of reactions. This "anion pool" method electrochemically generates strong nucleophiles from amine substrates. The amine nucleophiles then react with acid anhydrides to generate amides, and the by-product from this reaction undergoes further chemical transformations to generate pharmaceutically relevant benzoic esters. These one-pot reactions are operationally simple, are performed at room temperature, and avoid rare transition metals and added bases. The amide synthesis is amenable to primary and secondary amines and a variety of anhydrides with yields up to 90% obtained. Atom economy and process mass index (PMI) values calculated for this procedure indicate that this process can be considered greener compared to traditional amide synthesis routes used by industry. Furthermore, this electrochemical approach showed unique selectivity when substrates that contained two inequivalent amine moieties were examined.
HIGHLY CHEMOSELECTIVE REACTIONS IN PRESENCE OF AROMATIC AMINO GROUPS
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Page/Page column 39; 40, (2017/11/06)
: The invention discloses a novel process for highly chemoselective reactions of substituted anilines without any detectable reaction at aromatic amino group. The invention also relates to a novel process for preparation of neostigmine methylsulphate via chemoselective reaction of 3-amionphenol and aryl dimethylcarbamates.
Synthesis and Biological Evaluation of 2-Aminobenzothiazole and Benzimidazole Analogs Based on the Clathrodin Structure
Montalv?o, Sofia,Leino, Teppo O.,Kiuru, Paula S.,Lillsunde, Katja-Emilia,Yli-Kauhaluoma, Jari,Tammela, P?ivi
, p. 137 - 149 (2016/02/09)
A series of 2-aminobenzothiazole and benzimidazole analogs based on the clathrodin scaffold was synthesized and investigated for their antimicrobial and antiproliferative activities as well as for their effects in hepatitis C virus (HCV) replicon model. Compound 7, derived from 2-aminobenzothiazole, exhibited moderate antimicrobial activity only against the Gram-positive bacterium, Enterococcus faecalis. In the antiviral assay, compounds 4d and 7 were found to suppress the HCV replicon by >70%, but also to exhibit cytotoxicity against the host cells (35 and 44%, respectively). Compounds 4a and 7 demonstrated good activity in the antiproliferative assays on the human melanoma cell line A-375. To assess the selectivity of the effects between cancerous and noncancerous cells, a mouse fibroblast cell line was used. The IC50 values for compound 7 against the melanoma cell line A-375 and the fibroblast cell line BALB/c 3T3 were 16 and 71 μM, respectively, yielding fourfold selectivity toward the cancer cell line. These results suggest that compound 7 should be studied further in order to fully explore its potential for drug development. A series of novel 2-aminobenzothiazole and benzimidazole derivatives based on the clathrodin structure was synthesized and evaluated for antimicrobial, antiproliferative and antiviral activities. (9H-Fluoren-9-yl)-methyl [(2-aminobenzo[d]thiazol-6-yl)methyl]carbamate 7 exhibited antiproliferative activity against the melanoma cell line A-375 (IC50 = 16 μM) with 4-fold selectivity between cancerous (A-375) and noncancerous (BALB/c 3T3) cells.