Chlorotestosterone

Chlorotestosterone exhibits 50% of the androgenic and 100% of the anabolic activity of testosterone. 

Comparison of 17a-methyl-17)8-hydroxy-5a -androstano[3,2-r] pyrazole (D-l 1), 17a-methyl-17)8-hydroxyandrost-4-eno[3,2-c]pyrazole (A-157), and 17a-methyl-17/3-hydroxyandrost-4,6-dieno[3,2-c]pyrazole (A-168) showed that as the degree of unsaturation is increased there is a corresponding decrease in the anabolic and androgenic activities, with the last compound (A-168) having complete loss of these activities. It was suggested [124] that the anabolic and androgenic properties of this compound were lost due to the flattening imposed by the steroidal diene system. It was also found that introduction of an additional double bond between carbons 6 and 7 in 4-chlorotestosterone acetate (S-I48) results in the complete loss of activity (compare with S-146). 

All other 17-ester derivatives—4-chlorotestosterone 17-propionate (S-6), 17-succinate, 17-palmitate, 17-enantate, 17-phenylpropionate, 17-triphenylmethyl ether, 17-phenoxyacetate, and 17-cyclopentylpropionate [243] — were reported to be less active than 4-chlorotestosterone acetate. However, 4-chlorotestosterone chloroacetate was reported [263] to be several times more active than 4-chlorotestosterone acetate and 4-chlorotestosterone p-chlorophenoxyacetate was promising in showing a long lasting effect [234,263]. 

Chlorosiulfonic acid, 3, 139-140, 1127 methyl ester, 1123 2 -Chlorotestosterone, 1129 Chlorotetracycline, 1183 2-Chlorothiophene, 1129 m-Chlorotoluene, 212 o-Chlorotoluene, 212, 944 p-Chlorotoluene, 212, 870 2-Chloro-2,3,3-trifluorocyclobutyl acetate, 1271... 

Chlorotestosterone, 4-chloro-l 7fi-hyilroxyan-drost-4-en-3-ona an anabolic steroid obtained by partial synthesis from testosterone. Esters of 4-C. are used therapeutically, e.g. in convalescence, and for treatment of inflammation and tumors. 

A soln. of anhydrous chloral in anhydrous benzene added at room temp, to 4-chlorotestosterone, shaken until it dissolves and the product crystallizes 4 - chloro -17j - (1 - hydroxy -2,2,2- trichlorethoxy) androst -4- en -3- one. Y 9S%. R. Hiittenrauch, Arch. Pharm. 297, 124 (1964). 

ChloPO-/d -3-ketosteroids. 2 equivalents of sulfuryl chloride added drop wise at 20-25° during 5 min. to an agitated soln. of testosterone propionate in dry pyridine, and stirring continued for 30 min. — 4-chlorotestosterone propionate. Y 82.7%. F. e. s. H. Mori, Ghem. Pharm. Bull. 10, 429 (1962). 

A specific reagent used for the derivatization of keto groups is methoxylamine or ethoxylamine. The resulting derivative is a stable oxime. This derivatization can be used alone or in combination with silylation. Examples are described for boldenone [34] and chlorotestosterone (clostebol) [35 37]. 

Progesterone iso-1 Zearalenol- 3-3-TMS 2 -Methoxy-ethynylestradiol Progesterone iso-2 Chlorotestosterone (clostebol)... 

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