Antifertility compounds

A number of ethynyl steroids have been synthesized as potential suicide substrates in sterol biosynthesis or as potential antifertility compounds. In the former class were the 19-ethynyl-19-hydroxy-compounds (294) and (295) and the 17-(l-hydroxy-2-propynyl)-compounds (296) and (297). ° Among those in the latter class were the diethynyl-A-nor-compound (298), its 19-nor-ana-logue, and the 18-homo-analogue (299). A number of allenyl compounds... 

Thiirane is more bactericidal than oxirane, and derivatives of 2-mei captomethylthiirane inhibit tuberculosis. The following pharmacological uses have been reported for compounds derived from thiirane derivatives gold complexes of the adducts of diethylphosphine and thiirane (antiarthritic), adducts of thiiranes and malononitrile (antibacterial, blood vessel dilators, muscle relaxants, sedatives), thermolysis products of thiirane 1-oxides and adducts of thiirane 1-oxides with sulfenyl chlorides (antibacterial), adducts of 2,3-diarylthiirene 1,1-dioxides with ynamines (antibacterial, parasiticidal), adducts of 2,3-diarylthiirene 1,1-dioxides with enamines (antifertility), adducts of p-aminophenylacetic esters with thiirane (immunosuppressants), adducts of amines and thiiranes (radioprotective drugs). 

Antibiotic revolution has provided long and healthy life to people. The life expectancy has almost doubled. The increased population has caused many social problems in terms of food resources, environmental issues, employment, etc. To control these problems, population is required to be controlled. This has lead to the concept of family planning. Antifertility drugs are of use in this direction. Birth control pills essentially contain a mixture of S)mthetic estrogen and progesterone derivatives. Both of these compounds are hormones. It is known that progesterone suppresses ovulation. Synthetic progesterone derivatives are more potent than... 

The main use of progestins is based on their antifertility effect. Since progesterone is poorly absorbed, it cannot be given orally furthermore, it is not particularly potent and has an unacceptably short serum half-life of about 5 minutes. In early work, ethis-terone (5.39), an acetylenic compound prepared from androsterone, was an orally active progestin, but also had male hormone action. In subsequent work, a large number of... 

The Chinese reports that gossypol may act as an antifertility agent in men (218) have renewed Interest in this and related compounds. 

The dipyridyl-based contact herbicides (Diquat, Paraquat) exhibit antifertility effects on spermatocytes and cause fetal malformations. In addition these compounds are severely damaging to lungs, kidneys, liver, heart and/or QI tract, and can be permanently disabling when not lethal. 

From a synthetic standpoint, the most interesting silylated steroids are those having silicon substituted for one of the carbon atoms of a ring. Only one such system has been reported, that of the 6-silasteroids. A number of these compounds, for example 7, have been screened for estrogenic, antiestrogenic, and postcoital antifertility effects but no significant activity was noted (29). 

Disilamorpholines constitute another family of bioactive compounds. They have superior activity and are more easily prepared than their C-analogs. A series of compounds have been patented as muscle relaxants.506 4-(m-Methoxybenzyl)-l-oxa-4-aza-2,2,6,6-tetramethyl-2,6-disilacyclohexane, chosen for clinical muscle relaxant studies,479 was found to induce antifertility in male mammals (dogs). After administration of the drug (12-120 mg/kg daily) is stopped, their sperm count returns to normal and no evidence of testicular damage or aspermatogenesis is observed.507... 

The preparation of 2 -analogs of zoapatanol (67) from D-glucose was reported by van Boom and co-workers <01TL5749> (Scheme 50). These compounds may possess antifertility properties. 

Finally, an example of fluorination of the C = P bond has been reported." Reaction of the /1-oxido ylide 22 with gaseous perchloryl fluoride at — 35 C gives the fluoroalkenes 23A and B in 12 and 45 % yield, respectively. Alkene 23B is an intermediate in the synthesis of (-F)-13-fluoroprostaglandin methyl ester, a compound with antifertility and muscle-stimulating effects. 

A new type of. seco-ishwarane alcohol (724) has been identified in the roots of Aristolochia indica.326 This compound, which co-occurs with (+)-ledol (725), has antifertility properties when tested on mice. Its structure was deduced on the basis of spectral analysis together with its correlation with a derivative of ishwarane (726). A full report on the synthesis of ishwarone (727) has been presented.327... 

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