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Methyl Carbamate can cause cancer according to The National
Toxicology Program.Methyl carbamate appears as white
crystals,Methyl carbamate is a carbamate ester resulting from the
formal condensation of the carboxy group of carbamic acid with
methanol.
The carbamate group is a key structural motif in many approved
drugs and prodrugs. There is an increasing use of carbamates in
medicinal chemistry and many derivatives are specifically designed
to make drugtarget interactions through their carbamate moiety. In
this Perspective, we present properties and stabilities of
carbamates, reagents and chemical methodologies for the synthesis
of carbamates, and recent applications of carbamates in drug design
and medicinal chemistry.
Carbamate-bearing molecules play an important role in modern drug
discovery and medicinal chemistry. Organic carbamates (or
urethanes) are structural elements of many approved therapeutic
agents. Structurally, the carbamate functionality is related to
amide-ester hybrid features and, in general, displays very good
chemical and proteolytic stabilities. Carbamates are widely
utilized as a peptide bond surrogate in medicinal chemistry. This
is mainly due to their chemical stability and capability to
permeate cell membranes. Another unique feature of carbamates is
their ability to modulate inter- and intramolecular interactions
with the target enzymes or receptors. The carbamate functionality
imposes a degree of conformational restriction due to the
delocalization of nonbonded electrons on nitrogen into the carboxyl
moiety. In addition, the carbamate functionality participates in
hydrogen bonding through the carboxyl group and the backbone NH.
Therefore, substitution on the O- and N-termini of a carbamate
offers opportunities for modulation of biological properties and
improvement in stability and pharmacokinetic properties.
Carbamates have been manipulated for use in the design of prodrugs
as a means of achieving first-pass and systemic hydrolytic
stability. Carbamate derivatives are widely represented in
agricultural chemicals, such as pesticides,
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Grupo de productos : | Pharmaceutical intermediate |