Testosterone compounds

One of the side effects of testosterone compounds is masculinization in women (such as hirsutism, acne, depression of menses, and clitoral enlargement) and of their female offspring. Therefore, androgens are contraindicated in pregnant women. Prostatic hypertrophy may occur in males, which leads to urinary retention. Therefore, androgens are contraindicated in men with prostatic carcinoma. 

They are not excessively used in medicinal chemistry. Divinyl oxide is an excellent general anesthetic but it polymerizes easily and forms peroxides. Stabilization of the compound is usually achieved by addition of 0.01% of Ai-phenyl a-naphtylamine. On the other hand, compounds such as kainic acid, vinylbital, quinine, 17a-vinyl-testosterone, compound SKF 100 047, and vigabatrin (Figure 20.16) are perfectly stable vinyl derivatives. 

Because of these side effects, researchers have developed compounds that produce the same effects as those obtained from natural testosterone, but without the compound s harmful side effects. Some of those compounds increase the natural production of testosterone in the body when they are ingested. Others are derivatives of testosterone, compounds with similar chemical structures, but minor changes that reduce side effects. These derivatives include compounds such as dihydrotestosterone, androstenedione (also known as andro), dehy-droepiandrosterone (DHEA), clostebol, and nandrolone. Today most derivatives of testosterone and testosterone-producing compounds are banned by sports organizations, both because of their harmful side effects and because of the unfair advantages they provide athletes who use them. 

Under the reaction conditions (particularly if the hydrolysis solution is heated), water is lost in most cases to form the conjugated ketone product 65. This type of reaction was used to prepare steroids many years ago, and it remains an important method for the preparation of bicyclic ketones. The fundamental tetracyclic structure of a steroid is found in Chapter 1, where the hormonal steroids P-estradiol and testosterone (compounds labeled 32 and 33 in that chapter) are presented as examples of important organic compounds. 

Ketonic carbonyl groups are commonly encountered in steroids and their reduction is facile, even in the absence of an alcohol. The lithium-ammonia reduction of androsta-l,4-diene-3,17-dione affords androst-4-ene-3,17-dione in 20% yield but concurrent reduction of the C-17 ketone results in formation of testosterone in 40% yield, even though the reduction is performed rapidly at —40 to —60° and excess lithium is destroyed with solid ammonium chloride. Similar reduction of the C-17 carbonyl group has been observed in other compounds. In the presence of an alcohol, a ketone is complete-... 

Slight structural changes of the model compound testosterone may therefore further reduce the inherently low reactivity and favor the competition of... 

A highly modified methyl testosterone derivative also exhibits antiandrogenic activity. One synthesis of this compound Involves initial alkylation of methyl testosterone (3 ) by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative Formylation with alkoxide and... 

To a solution of 1 g of the mixture of 3-ketal-isomers of compound (II) in 10 cc of acetic anhydride is added a solution of 700 mg of p-toluenesulfonic acid in 7 cc of ecetic anhydride. The reaction mixture is kept at room temperature and under stirring for 5 hours. After some time e crystalline product begins to precipitate and the precipitation is complete by diluting with water. The precipitate is filtered and crystallized from methanol to give 17a-ethynvl-19-nor-testosterone 3,17-diecetate (III), melting point 175°C to 17B°C. 

Polycyclic compounds are common in nature, and many valuable substances have fused-ring structures. For example, steroids, such as the male hormone testosterone, have 3 six-membered rings and 1 five-membered ring fused together. Although steroids look complicated compared with cyclohexane or decalin, the same principles that apply to the conformational analysis of simple cyclohexane lings apply equally well (and often better) to steroids. 

The strains described in Table 9.4 are all of commerdal value since they produce compounds which are either pharmacologically active or can be converted to pharmacologically important compounds. For example, the production of 1,4-androstadiene-3,17-dione from (5-sitosterol provides material which can be readily converted to estrone, while 4-androstene-3,l 7-dione can be converted to testosterone. 

The chemical formula of a compound represents its composition in terms of chemical symbols. Subscripts show the numbers of atoms of each element present in the smallest unit that is representative of the compound. For molecular compounds, it is common to give the molecular formula, a chemical formula that shows how many atoms of each type of element are present in a single molecule of the compound. For instance, the molecular formula for water is H20 each molecule contains one O atom and two H atoms. The molecular formula for estrone, a female sex hormone, is Clgl-I2202, showing that a single molecule of estrone consists of 18 C atoms, 22 FI atoms, and 2 O atoms. A molecule of a male sex hormone, testosterone, differs by only a few atoms its molecular formula is (lyH2802. Think of the consequences of that tiny difference ... 

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