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Thioamide

thioamide drugs, thioamide mechanism of action
A thioamide rarely, thionamide, but also known as thiourylenes is a functional group with the general structure R–CS–NR′R″, where R, R′, and R″ are organic groups They are analogous to amides but they exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier One of the best-known thioamides is thioacetamide, which is used as a source of the sulfide ion and is a building block in heterocyclic chemistry

Thioamides or anti-thyroid drugs are also a class of drugs that are used to control thyrotoxicosis

Preparation and structure

Thioamides are typically prepared by treating amides with phosphorus sulfides such as phosphorus pentasulfide and, in more specialized applications, Lawesson's reagent An alternative route entails the reaction of nitriles with hydrogen sulfide The Willgerodt-Kindler reaction also affords benzylthioamides

Thioamides in biochemistry and medicine

Thioamides are also a class of drugs that are used to control thyrotoxicosis

Thioamides have been incorporated into peptides as isosteres for the amide bond Peptide modifications are analogues of the native peptide, which can reveal the structure-activity relationship SAR Analogues of peptides can also be used as drugs with an improved oral bioavailability Thioamides inhibit the enzyme thyroid peroxidase in the thyroid, reducing the synthesis of triiodothyronine T3 and thyroxine T4, thereby blocking uptake of iodotyrosines from the colloid They also block iodine release from peripheral hormone Maximum effects occur only after a month, since hormone depletion is caused by reduced synthesis, which is a slow process

Because thioamides can penetrate the placental barrier, caution is advised when used during pregnancy Ten percent of patients report skin eruptions such as macules and papules, urticaria, dermatitis, fever, and arthralgia; 003% of all patients develop agranulocytosis

Members of the thioamide group include methimazole, carbimazole converted in vivo to methimazole, and propylthiouracil

References

  1. ^ Wiberg, Kenneth B; Rablen, Paul R 1995 "Why Does Thioformamide Have a Larger Rotational Barrier Than Formamide" J Am Chem Soc 117 8: 2201–2209 doi:101021/ja00113a009 
  2. ^ Gompper, R; Elser, W 1973 "2-Methylmercapto-N-Methyl-Δ2-Pyrroline" Organic Syntheses ; Collective Volume, 5, p 780 
  3. ^ Schwarz, George 1955 "2,4-Dimethylthiazole" Organic Syntheses ; Collective Volume, 3, p 332 
  4. ^ Rolfs, Andreas; Liebscher, Jürgen 1998 "3-Morpholino-2-Phenylthioacrylic Acid Morpholide and 5-4-Bromobenzoyl-2-4-Morpholino-3-Phenylthiophene" Organic Syntheses ; Collective Volume, 9, p 99 
  5. ^ Artis, Dean R; Lipton, Mark A 1998 "Conformations of Thioamide-Containing Dipeptides: A Computational Study" J Am Chem Soc 120: 12200–12206 doi:101021/ja982398t 


thioamide, thioamide drugs, thioamide effects on fetus, thioamide glycine, thioamide groups, thioamide mechanism of action, thioamide propylthiouracil, thioamide structure, thioamide synthesis, thioamide therapy


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Thioamide


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    29.10.2014


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