Design and Synthesis of New Steroid-cyclobutanone Derivative

Abstract

S i n c e s eve ra l ye a r s a g o, d i ve r s e corticosteroid derivatives have been development; for example, the synthesis 3α-acetoxy-16α

Retracted: Design and synthesis of a bismethylsulfanyl‐steroid‐azetyl butanol derivative from 2‐nitroestradiol

“…Other reports display the preparation of a hexynyl‐triazonine derivative through contraction of ring A from testosterone followed by the addition of 2‐(4‐nitro‐phenyl)‐4,5‐dihydro‐1H‐[1,3,6]triazonine to steroid . Recently, a polycyclic‐imidizalone derivative was prepared from testosterone and 2‐methylimidazol . All these data showed the synthesis of several steroid‐polycyclic derivatives; however, several protocols use some reagents that require special conditions.…”

Design and Synthesis of a New Androgen Derivative using Some Strategies

“…Finally, the presence of compound 5was further confirmed from mass spectrum which showed a molecular ion at m/z 522.30. The third stepwas achieved bythe synthesisof7(Chloro-acetic acid 3-((3-chloro-2-oxocyclobutyl)-{2-[(3-chloro-2-oxo-cyclobutyl)- [1,10] phenanthrolin-5-ylmethyl-amino]ethyl}-amino)-10,13-dimethyl-2, 3,6,7,8,9,10,11,12, 13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester)byreactionof 5with chloroacetylchloride in the presenceoftriet-hylamine.This method has been previously reported for other type of compound withbothaminoand iminogroupsinvolved in its structure chemical, which react with chloroacetylchloride to form cyclobutanone groups 16 .However, it isnoteworthy that hydroxylgroupof compound 5 was esterified with acetylchloride. This phenomenon is similar to esterification of other type of compounds 17,18 .…”

“…Other data indicate the preparation of 17-(2-[[(2-hydroxy-naphtalen-1-yl)phenyl-methyl]-amino]ethyl amino)-10,13-dimethyl-2,2,6,7,8,9,10,11,12,13, 14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthren-3-ol by the reaction between 1-[(2-amino-ethylamino)-phenyl-methyl]-naphthalen-2-ol and androsterone using boric acid as catalyst 5 . Additionally, other androgen (Succinic acid mono-{6-[(2-amino-ethylamino)-methyl]-1-ethinyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b, 11,12,12a-dodecahydro-1H-7-oxa-8-aza-dicyclopenta-[a,h]-phenanthren-1-yl}ester) was prepared by reaction of hemisuccinate of danazol with ethylenediamine hydrochloride in presence of formaldehyde 6 .Also Other report [7][8][9] indicate the preparation of 17²-(N-Acetyl-42 -imidazolyl)-3-acetoxyandrost-5-ene by the reaction of 17-(42 -Imidazolyl)androst-5-en-3²-ol in pyridine/Ac 2 O.All these experimental results show several procedures which are available for synthesis of diverse androgen derivatives; nevertheless, expensive reagents and special conditions are required.…”

Design and Synthesis of Three Naphthol Derivatives Using Several Strategies

“…Additionally, other naphthol derivative [N-{3-mercapto-5-(naphthalen-1-yl)-4H-1,2,4-triazol-4-yl}benzamide] was synthesized by the reaction of potassium 2-(2-naphthoyl)hydrazine carbodithioate with N-aminoarylcarboxamides in ethanol to reflux 9 . The compound N-(2-{[(2-hydroxy-naphtalen-1-yl)-phenyl-methyl]-amino}-ethyl)-3,4-dinitrobenzamide was synthesized by the reaction of 1-[(2-amino-ethylamino)-phenyl-methyl]naphthalen-2-ol with 3,5-dinitrobenzoic acid using 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide or boric acid as catalyst 10 . All these experimental results show several procedures that are available for synthesis of naphthol derivatives.…”

“…26, No. 18 (2014), [6001][6002][6003][6004] phenanthren-3-ol), 5 (1-[[(2-aminoethyl)amino]-(phenyl) methyl]-2-naphthol) and (4-allyl-2-methoxyphenyl 4-[(2aminoethyl)amino]-4-oxobutanoate) were prepared according to a reported method 10,11 . The other compounds used in this study were purchased from Sigma-Aldrich Co., Ltd.…”