19-Hydroxy-5β,19-cyclosteroids: synthesis, isomerization and ring opening

Templeton, J. F.; Ling, Y.; Lin, Weiyang; Majgier‐Baranowska, Helena; Marat, Kirk

doi:10.1039/a604405k

Cited by 6 publications

(2 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, 6β-hydroxy-3α,5-cyclo-5α-androstan-17-one (149), and other analogues (150, 151 and 158) were synthesized as steroidal blood pressure-lowering hormones [160,161]. Cyclosteroids (152 and 153), which show an anabolic effect, were synthesized from 19-nor steroids, and would be of great interest for sports medicine as representatives of anabolic steroids [162,163], although other cyclosteroids (154)(155)(156)(157) were synthesized as potential agents with antitumor properties [164][165][166].…”

Section: Sterols and Triterpenoids With Cyclopropane Ring In The Side Chainmentioning

confidence: 99%

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

2021

View full text Add to dashboard Cite

This review focuses on the rare group of carbon-bridged steroids (CBS) and triterpenoids found in various natural sources such as green, yellow-green, and red algae, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in amoebas, fungi, fungal endophytes, and plants. For convenience, the presented CBS and triterpenoids are divided into four groups, which include: (a) CBS and triterpenoids containing a cyclopropane group; (b) CBS and triterpenoids with cyclopropane ring in the side chain; (c) CBS and triterpenoids containing a cyclobutane group; (d) CBS and triterpenoids containing cyclopentane, cyclohexane or cycloheptane moieties. For the comparative characterization of the antitumor profile, we have added several semi- and synthetic CBS and triterpenoids, with various additional rings, to identify possible promising sources for pharmacologists and the pharmaceutical industry. About 300 CBS and triterpenoids are presented in this review, which demonstrate a wide range of biological activities, but the most pronounced antitumor profile. The review summarizes biological activities both determined experimentally and estimated using the well-known PASS software. According to the data obtained, two-thirds of CBS and triterpenoids show moderate activity levels with a confidence level of 70 to 90%; however, one third of these lipids demonstrate strong antitumor activity with a confidence level exceeding 90%. Several CBS and triterpenoids, from different lipid groups, demonstrate selective action on different types of tumor cells such as renal cancer, sarcoma, pancreatic cancer, prostate cancer, lymphocytic leukemia, myeloid leukemia, liver cancer, and genitourinary cancer with varying degrees of confidence. In addition, the review presents graphical images of the antitumor profile of both individual CBS and triterpenoids groups and individual compounds.

show abstract

Section: Sterols and Triterpenoids With Cyclopropane Ring In The Side Chainmentioning

confidence: 99%

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

2021

View full text Add to dashboard Cite

show abstract

“…96 Derivatives of androst-5-ene-7,17-dione 43 have also been studied as inhibitors of aromatase. 97 Various 19-hydroxy-5b,19-cyclosteroids 98 and 19-hydroxy-1b,19-cyclosteroids 99 have been synthesized by reductive cyclization of 19-formyl-4-en-3-ones (44?45) and 19-formyl-1-en-3-ones (46?47) and their biological activity has been examined in this context. The ring opening reactions of these 5b,19-cyclosteroids have been studied.…”

Section: Androgensmentioning

confidence: 99%