Practical synthesis of a chromene analog for use as a retinoic acid receptor alpha antagonist lead compound

Jetson, Rachael; Malik, Neha; Luniwal, Amarjit; Chari, Venkatesh; Ratnam, Manohar; Erhardt, Paul

doi:10.1016/j.ejmech.2013.02.012

Cited by 5 publications

(2 citation statements)

References 11 publications

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“…9 The approach to address a specific construction of the A 1 -A ring system of GLY II at the start of the synthesis is depicted in retrosynthetic Scheme 3. On the basis of a literature precedent, 11,12 this involves manipulating 7-hydroxycoumarin to form the target ring system and then takes advantage of the previous model chemistry to produce a keto-aldehyde that is poised for an intramolecular benzoin condensation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Total Synthesis of (±)-Glyceollin II and a Dihydro Derivative

2015

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Stressed soybeans produce a group of phytoalexins that belong to the 6a-hydroxypterocarpan family of flavonoids. Certain of the more prominent members, such as the glyceollins I, II, and III, have demonstrated potential antidiabetic properties and promising cytotoxicity in both human breast and prostate cancer cell cultures with preliminary studies in animals further demonstrating antitumor effects in estrogen-dependent, human breast cancer cell implants. Although syntheses of glyceollin I have been reported previously, this work constitutes the first total directed synthesis of (±)-glyceollin II. It involves 12 steps with an overall yield of 7% using practical methods that should be readily scalable to produce quantities needed for advanced biological characterization. Highlights include a novel intramolecular benzoin condensation, a chelation-controlled lithium aluminum hydride-mediated reduction, and an intramolecular cyclization via the formation of a transient epoxide intermediate to cap the construction of the 6a-hydroxypterocarpan system. Additionally, a dihydro analogue has been obtained, and several isolated intermediates have been made available for evaluation of their biological properties and possible contributions toward elaborating key structure-activity relationship data among this family of promising phytoalexins elicited from stressed soybeans.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Total Synthesis of (±)-Glyceollin II and a Dihydro Derivative

2015

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“…Other authors have described the synthesis of novel monofluoro lead compound 2‐fluoro‐4‐[8‐bromo‐2,2‐dimethyl‐4‐(4‐methylphenyl)‐chromen‐6‐yl]‐4‐aminocarbonylbenzoic acid as selective RARα antagonist. Antagonist effects of this fluoro compound were evaluated on the classical ligand‐sensitive promoter activation by RARα in MCF7 breast cancer cells .…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of New 2H‐Chromene Retinoids Hybrid Derivatives by Suzuki Cross‐coupling Reactions

Kaoukabi

Belachemi

Lahcini

et al. 2019

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).In an attempt to improve anticancer activity, a series of retinoids-chromene hybrids was described. The novel heterocyclic chromene-retinoids hybrid including oxygen as a heteroatom in a six-membered cyclic ring (2H-chromene or 2H-1-benzopyran) was designed and synthesized by introducing different groups such as an aromatic or styrylphenyl ring in 6-position of 2H-chromene. These novel compounds were synthesized by using the efficient cascades one-pot process involving Wittig-Horner-Emmons reaction and Suzuki-Miyaura cross-coupling pallado-catalyzed reactions with 60% to 90% overall yields. These new compounds were tested against glioblastoma multiforme brain cancer, medulloblastoma, neuroblastoma cell lines, and breast cancer MCF-7 cell lines. Two of them exhibited an appreciable anti-tumor activity in the low micromolar range, which opens new perspectives for therapeutic application on humans.

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Preparation, characterization and use of sulfonylbis(1,4-phenylene)bis(sulfamic acid) as an eco-benign, efficient, reusable and heterogeneous catalyst for the synthesis of mono- and bis-chromenes

Mahmoodi

2017

J IRAN CHEM SOC

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Practical synthesis of a chromene analog for use as a retinoic acid receptor alpha antagonist lead compound

Cited by 5 publications

References 11 publications

Total Synthesis of (±)-Glyceollin II and a Dihydro Derivative

Total Synthesis of (±)-Glyceollin II and a Dihydro Derivative

Efficient Synthesis of New 2H‐Chromene Retinoids Hybrid Derivatives by Suzuki Cross‐coupling Reactions

Preparation, characterization and use of sulfonylbis(1,4-phenylene)bis(sulfamic acid) as an eco-benign, efficient, reusable and heterogeneous catalyst for the synthesis of mono- and bis-chromenes

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