Synthesis and biological activities of organoaluminum steroids

Abstract

This review presents the synthesis of organoaluminum steroids (OAS) using catalytic cycloalumination of vinylcholestane and/or allylcholestane derivatives with Et 3 Al catalyzed by Cp 2 ZrCl 2 which gives aluminacyclopentanes in a yield of about 90 %. Biological activity of synthesized organoaluminum steroids was determined with an aid of PASS program. Organoaluminum steroids showed antiprotozoal, antihypercholesterolemic, and antieczematic activity with a certainty from 78 to 92 %. Scheme 1: Reagents and conditions: i. PCC (pyridiniumchlorochromate), Al 2 O 3 , C 6 H 6 (81 %); ii. Ph 3 P=CH 2 , DMSO, C 6 H 6 (88 %); iii. Cl 3 CCOCl, Zn (64 %); iv. Zn, AcOH; v. Ph 3 P=CH 2 , DMSO, C 6 H 6 (74 %); vi. Cp 2 ZrCl 2 , Et 3 Al; vii. CuSO 4 /SiO 2 (72 %) Scheme 2: Synthesis of compound 15. Reagents and conditions: i. PCC (pyridiniumchlorochromate)-Al 2 O 3 , C 6 H 6 (81 %); ii. Ph 3 P=CHCH 2 SiMe 3 , THF (85 %); iii. BF 3 /AcOH (89 %); iv. Et 3 Al (3 eq.), Cp 2 ZrCl 2 (10 %)

Steroids Bearing Heteroatom as Potential Drugs for Medicine

“…Aluminum-containing steroids (202)(203)(204)(205)(206)(207)(208)(209), as depicted in Figure 30, represent a unique class of chemical compounds that have been synthesized and extensively studied. Their biological activity has been investigated and reported in various research articles [280][281][282][283][284]. These aluminum-containing steroids exhibit distinctive properties and activities.…”

“…Their utilization aids in advancing scientific knowledge, exploring new therapeutic possibilities, and driving innovation in drug development. Table 19 provides an overview of the structures and biological activities of the organotin steroids (281)(282)(283)(284)(285)(286)(287)(288)(289)(290)(291)(292)(293)(294)(295)(296)(297)(298). These compounds have shown diverse biological effects, highlighting their potential In therapeutic applications.…”

“…Organotin steroids (281)(282)(283)(284)(285)(286)(287)(288)(289)(290)(291)(292)(293)(294)(295)(296)(297)(298), as depicted in Figure 45, were synthesized via the re-action of various organotin reagents with steroids [358][359][360]. These synthetic steroids have exhibited remarkable properties, including inhibiting the growth of malignant tumors, as well as being employed as insecticides, larvicides, bactericides, and fungicides [341,342,[358][359][360][361][362][363].…”

“…Biological activities of steroids bearing aluminum atom(202)(203)(204)(205)(206)(207)(208)(209) [284].…”

“…Biological activities of steroids bearing tin atom(281)(282)(283)(284)(285)(286)(287)(288)(289)(290)(291)(292)(293)(294)(295)(296)(297)(298) [358].…”