<i>cis</i>-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

Gogoi, Dimpee; Devi, Rajlakshmi; Pahari, Pallab; Sarma, Bipul; Das, Sajal Kumar

doi:10.3762/bjoc.12.280

Cited by 9 publications

(5 citation statements)

References 30 publications

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“…Furthermore, IVc should enjoy enhanced hyperconjugative stabilization compared to IVa and IVb . Notably, this impressive cis-diastereoselectivity complements observations made by us and others ,, in the FC ring closure onto a tetralin system.…”

Section: Resultssupporting

confidence: 82%

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Das

2022

J. Org. Chem.

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Presented herein is a BF 3 •OEt 2 -mediated, diastereoselective one-pot double cyclization of 4-aryl-2-[(arylthio)methyl]butanals leading to the formation of cis-tetrahydro-6H-naphtho[2,1-c]thiochromenes for the first time. Mechanistically, the formation of the title products involves the one-pot intramolecular Friedel−Crafts hydroxyalkylation/intramolecular Friedel−Crafts alkylation cascade. This synthetic methodology is featured by its high atom economy, broad substrate scope, mild transition-metalfree reaction conditions, capability to assemble two new rings in one pot, and moderate to high yields (up to 94% yield). It was then applied in the synthesis of a thia analogue of brazilane and a chromeno[3,4-c]chromene derivative. Moreover, the methodology was successfully extended to the synthesis of cis-hexahydrobenzo[c]phenanthrenes. Specifically, 1,5-diarylpentan-3-ones were first subjected to the Corey−Chaykovsky reaction, and the resulting epoxides, without being chromatographically isolated, were treated with BF 3 •OEt 2 to afford the cyclized products in high yields (up to 84% yield over two steps).

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Section: Resultssupporting

confidence: 82%

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Das

2022

J. Org. Chem.

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“…1 H and 13 C-NMR spectra of 1 , which revealed three segments, viz. a benzochroman backbone and two glucosyl groups ( Table 1 , Supplementary Materials ), respectively [ 14 ]. Signals corresponding to an ABCD system (1,2-disubstituted aromatic ring) were observed at δ H 8.27 (d, J = 7.5 Hz, H-9), 8.25 (d, J = 7.5 Hz, H-6), 7.27 (t, J = 7.5 Hz, H-7), and 7.19 (t, J = 7.5 Hz, H-8).…”

Section: Resultsmentioning

confidence: 99%

Isolation and Identification of Benzochroman and Acylglycerols from Massa Medicata Fermentata and Their Inhibitory Effects on LPS-Stimulated Cytokine Production in Bone Marrow-Derived Dendritic Cells

et al. 2018

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Massa Medicata Fermentata (MMF), known as Shenqu, is an important traditional Chinese medicine widely used to treat indigestion, vomiting, and diarrhea. In this study, a new benzochroman, 3(S)-3,4-dihydro-5,10-di-β-d-glucopyranoside-2,2-dimethyl-2H-naphtho(2,3-b)pyran-3-ol (1), and five known galactosyl acylglycerols (2–6) were isolated from a methanol extract from MMF. In addition, their chemical structures were determined by chemical and spectroscopic methods, which were compared with the previously reported data. Furthermore, the effects of isolated compounds on lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells were investigated. Compounds 1–3 exhibited significant inhibitory effects on the LPS-induced production of IL-6 and IL-12 p40, with IC50 values ranging from 1.6 to 10.2 μM. Compounds 2 and 3 also exhibited strong inhibitory effects on the LPS-stimulated production of TNF-α with IC50 values of 12.0 and 11.2 μM, respectively. The results might provide a scientific basis for the development of the active components in MMF, as well as for novel anti-inflammatory agents.

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“…52 Analogs of brazilin have been also proposed. 53 There are different options to modulate the original structure of BRZ. It will be interesting to determine if their enhanced anticancer activity can derive from their capacity to interfere with the functioning of BAF1 in cell nuclei.…”

Section: Discussionmentioning

confidence: 99%

“…Analogs of brazilein with greater antitumor potential have been designed and synthesized 52 . Analogs of brazilin have been also proposed 53 . There are different options to modulate the original structure of BRZ.…”

Section: Discussionmentioning

confidence: 99%

Molecular docking of brazilin and its analogs to barrier‐to‐autointegration factor 1 (BAF1)

Soeiro

Vergoten

Bailly

2022

Annals of the New York Academy of Sciences

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The tetracyclic phenolic compound brazilin, derived from the wood of Caesalpinia sappan, has been shown to bind to the chromatin protein BAF1 (barrier-to-autointegration factor 1), a protein essential to maintain integrity of the nuclear envelope in cells. BAF1 plays a role in cancer development. Using molecular docking, we have located the binding site for brazilin on the surface of the BAF1 monomer and compared its binding to that of four analogs. The oxidized product brazilein ( E = −57.7 kcal/mol) exhibits a higher affinity for BAF1 compared to the reduced form brazilin ( E = −38.2 kcal/mol). Incorporation of a 4-hydroxyl substituent on the indenochromene unit affords hematoxylin and hematein. In silico analysis predicts that the oxidized form hematein ( E = −66.2 kcal/mol) displays a higher affinity for BAF1 than the reduced form hematoxylin ( E = −42.2 kcal/mol). In contrast, the atypical bis-lactone product brazilide A cannot form good complexes with BAF1. The analysis points to the formation of more stable BAF1 complexes with the oxidized molecules compared to the reduced ones, but the position of the binding site on the protein cavity is different for brazilin/hematoxylin compared to brazilein/hematein. Our study may be useful to guide the design of BAF1 ligands.

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cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

Cited by 9 publications

References 30 publications

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Isolation and Identification of Benzochroman and Acylglycerols from Massa Medicata Fermentata and Their Inhibitory Effects on LPS-Stimulated Cytokine Production in Bone Marrow-Derived Dendritic Cells

Molecular docking of brazilin and its analogs to barrier‐to‐autointegration factor 1 (BAF1)

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