Naturally Occurring Aromatic Steroids

Taub, D.

doi:10.1002/9780470129654.ch4

Cited by 6 publications

(4 citation statements)

References 112 publications

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“…The presence of one or more aromatic rings in these steroids imparts unique chemical and biological properties, making them of particular interest in various fields of research, including medicinal chemistry and drug discovery. Steroids bearing aromatic rings represent a fascinating subgroup of steroids that possess distinct chemical and biological characteristics [22][23][24]. Their unique structural features and diverse pharmacological profiles make them promising candidates for drug development and therapeutic applications.…”

Section: Steroids Bearing Aromatic Ring(s)mentioning

confidence: 99%

“…Natural steroids and triterpenoids that contain one or more aromatic rings in their structure are referred to as aromatic steroids. They are a diverse group of lipid molecules synthesized by bacteria, fungi, plants, invertebrates, and animals [21][22][23][24][25][26]. These aromatic steroids have been identified in various sources, including geological samples, marine sediments, and oil [27][28][29][30][31].…”

Section: Steroids Bearing Aromatic Ring(s)mentioning

confidence: 99%

“…Steroids bearing aromatic rings are a distinct subgroup within the larger family of steroids, which are characterized by their fused ring structure [ 21 , 22 , 23 ]. The presence of one or more aromatic rings in these steroids imparts unique chemical and biological properties, making them of particular interest in various fields of research, including medicinal chemistry and drug discovery.…”

Section: Steroids Bearing Aromatic Ring(s)mentioning

confidence: 99%

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Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Dembitsky

2023

Molecules

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This review delves into the investigation of the biological activity and structural diversity of steroids and related isoprenoid lipids. The study encompasses various natural compounds, such as steroids with aromatic ring(s), steroid phosphate esters derived from marine invertebrates, and steroids incorporating halogen atoms (I, Br, or Cl). These compounds are either produced by fungi or fungal endophytes or found in extracts of plants, algae, or marine invertebrates. To assess the biological activity of these natural compounds, an extensive examination of referenced literature sources was conducted. The evaluation encompassed in vivo and in vitro studies, as well as the utilization of the QSAR method. Numerous compounds exhibited notable properties such as strong anti-inflammatory, anti-neoplastic, anti-proliferative, anti-hypercholesterolemic, anti-Parkinsonian, diuretic, anti-eczematic, anti-psoriatic, and various other activities. Throughout the review, 3D graphs illustrating the activity of individual steroids are presented alongside images of selected terrestrial or marine organisms. Additionally, the review provides explanations for specific types of biological activity associated with these compounds. The data presented in this review hold scientific interest for academic science as well as practical implications in the fields of pharmacology and practical medicine. The analysis of the biological activity and structural diversity of steroids and related isoprenoid lipids provides valuable insights that can contribute to advancements in both theoretical understanding and applied research.

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Section: Steroids Bearing Aromatic Ring(s)mentioning

confidence: 99%

Section: Steroids Bearing Aromatic Ring(s)mentioning

confidence: 99%

Section: Steroids Bearing Aromatic Ring(s)mentioning

confidence: 99%

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Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Dembitsky

2023

Molecules

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“…[19] The construction of five-membered rings is much more difficult because it does not arise from the natural reactivity pattern of common functional groups that are prone to construct six-membered rings. Accordingly, entirely new concepts of how to modulate chemical reactivity were introduced and refined to practical synthetic methods.…”

Section: How Do You View the Historical Development Of Organic Synmentioning

confidence: 99%

Organic Synthesis: Wherefrom and Whither? (Some Very Personal Reflections)

Denmark

2017

Israel Journal of Chemistry

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This perspective represents a (highly personal) examination of the past, present and future of synthetic organic chemistry. The central thesis posits that the confluence of factors that led to the “Golden Age of Natural Product Synthesis” in the second half of the twentieth century can be traced back to the identification of the therapeutic potential of steroid hormones culminating in the introduction of oral contraceptives. The tremendous benefits of those activities to the development of organic synthesis as a vibrant discipline led to the exponential increase in strategies and methods and the ability to tackle, larger and larger molecules of greater and greater complexity. The existential challenge to the health of organic synthesis is whether a similarly dynamic future can be anticipated and if so, to what end and how. Musings on potential answers to those questions are presented.

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A Highly Stereoselective Synthesis of C(11)‐Functionalized Aromatic Steroids by an Intramolecular Benzocyclobutene‐Olefin ‐Cycloaddition. Preliminary Communication

Oppolzer

Petrzilka

Bättig

1977

Helvetica Chimica Acta

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SummaryThe racemic cis-anti-trans-steroids 9 to 11 have been synthesized in a highly stereoselective manner starting from 4-methoxybenzocyclobutene carboxylic acid via the key step 8 -+ 9. (cf. Scheme 2).The total synthesis of steroids is a continuing challenge for the organic chemist. From 1939 up to the present numerous often exciting and even some practical routes to this pharmaceutically important class of compounds have been developed1). Based on our pioneering work on intramolecular quinodimethane cycloadditions [6-81 a new approach to this skeleton via the generalized sequence I + I T --f 111 (Scheme 1)appeared feasible. Consideration of models of all four possible transitions states for the intramolecular cycloaddition of 11, points towards kinetically favoured formation of adducts I11 with anti-disposed H-C(8) and H-C( 14), caused by steric interactions of the angular methyl group. In addition, one may expect [7] that the trans-or cis-B,C-ring fusion in I11 will be controlled by the influence of a sp3-or sp2-carbon functional group C = Z on the endolexo mode of the addition I1 -+ 111. In fact, highly stereoselective formation of trans-anti-trans products has been observed in a related I)Reviews: [l-51.

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Naturally Occurring Aromatic Steroids

Cited by 6 publications

References 112 publications

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Organic Synthesis: Wherefrom and Whither? (Some Very Personal Reflections)

A Highly Stereoselective Synthesis of C(11)‐Functionalized Aromatic Steroids by an Intramolecular Benzocyclobutene‐Olefin ‐Cycloaddition. Preliminary Communication

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