An efficient route for annulation of pyrimidines to steroids and non-steroids via a base catalyzed one-pot three component reaction

Saikia, Pallabi; Gogoi, Shyamalee; Gogoi, Sanjib; Boruah, Romesh C.

doi:10.1016/j.steroids.2014.06.015

Cited by 11 publications

(10 citation statements)

References 17 publications

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“…Particularly, the incorporation of different heterocyclic rings into the steroid nucleus has been recognized as a useful strategy to generate new steroidal derivatives for biological screenings [26,27] . In this sense, we have previously shown that after the oxidative cleavage of ring A of a 3‐oxo‐Δ 4 ‐steroid, the resulting secosteroid can participate as a bifunctional building block in a three‐component‐4‐center Ugi reaction (Ugi‐3CR) to yield an azasteroid in which a nitrogen atom is incorporated into the steroidal nucleus, with the concomitant formation of a quaternary stereocenter [28] .…”

Section: Resultsmentioning

confidence: 99%

Beyond Pseudo‐natural Products: Sequential Ugi/Pictet‐Spengler Reactions Leading to Steroidal Pyrazinoisoquinolines That Trigger Caspase‐Independent Death in HepG2 Cells

et al. 2021

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In this work, we describe how stereochemically complex polycyclic compounds can be generated by applying a synthetic sequence comprising an intramolecular Ugi reaction followed by a Pictet‐Spengler cyclization on steroid‐derived scaffolds. The resulting compounds, which combine a fragment derived from a natural product and a scaffold not found in nature. are both structurally distinct and globally similar to natural products at the same time, and interrogate an alternative region of the chemical space. One of the new compounds showed significant antiproliferative activity on HepG2 cells through a caspase‐independent cell‐death mechanism, an appealing feature when new antitumor compounds are searched.

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Section: Resultsmentioning

confidence: 99%

Beyond Pseudo‐natural Products: Sequential Ugi/Pictet‐Spengler Reactions Leading to Steroidal Pyrazinoisoquinolines That Trigger Caspase‐Independent Death in HepG2 Cells

et al. 2021

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“…Although there is an example of condensation using β-enamino ketones (Xu et al, 2012 ). Boruah group have developed a range of methods, among which are three-component condensation of steroidal ketones with aromatic aldehydes and amidine derivatives in presence of potassium tert-butoxide (Saikia et al, 2014 ), Pd(OAc) 2 -catalyzed hetrocyclization of steroidal β-halo-α,β-unsaturated aldehydes with amidines (Gogoi et al, 2013 ) and SmCl 3 -catalyzed condensation of β-formyl enamide with urea under microwave irradiation (Barthakur et al, 2007 ). Baran group reported synthesis of 4,5-disubstituted pyrimidines from steroidal ketones and formamidine acetate (Baran et al, 2006 ).…”

Section: Discussionmentioning

confidence: 99%

Steroidal Pyrimidines and Dihydrotriazines as Novel Classes of Anticancer Agents against Hormone-Dependent Breast Cancer Cells

et al. 2018

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Most breast and prostate tumors are hormone-dependent, making it possible to use hormone therapy in patients with these tumors. The design of effective endocrine drugs that block the growth of tumors and have no severe side effects is a challenge. Thereupon, synthetic steroids are promising therapeutic drugs for the treatment of diseases such as hormone-dependent breast and prostate cancers. Here, we describe novel series of steroidal pyrimidines and dihydrotriazines with anticancer activities. A flexible approach to unknown pyrimidine and dihydrotriazine derivatives of steroids with selective control of the heterocyclization pattern is disclosed. A number of 18-nor-5α-androsta-2,13-diene[3,2-d]pyrimidine, androsta-2-ene[3,2-d]pyrimidine, Δ1, 3, 5(10)-estratrieno[16,17-d]pyrimidine, and 17-chloro-16-dihydrotriazine steroids were synthesized by condensations of amidines with β-chlorovinyl aldehydes derived from natural hormones. The synthesized compounds were screened for cytotoxicity against breast cancer cells and showed IC50 values of 7.4 μM and higher. Compounds were tested against prostate cancer cells and exhibited antiproliferative activity with IC50 values of 9.4 μM and higher comparable to that of cisplatin. Lead compound 4a displayed selectivity in ERα-positive breast cancer cells. At 10 μM concentration, this heterosteroid inhibited 50% of the E2-mediated ERα activity and led to partial ERα down-regulation. The ERα reporter assay and immunoblotting were supported by the docking study, which showed the probable binding mode of compound 4a to the estrogen receptor pocket. Thus, heterosteroid 4a proved to be a selective ERα modulator with the highest antiproliferative activity against hormone-dependent breast cancer and can be considered as a candidate for further anticancer drug development. In total, the synthesized heterosteroids may be considered as new promising classes of active anticancer agents.

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“…The conventional method is commonly used to synthesize steroid-pyrimidines (6) via one-pot under reflux with the aid of potassium tertiary butoxide base to condense ketone and aldehyde in ethanol to achieve 68%-82% yield. [167] The metal-free condition has been utilized to achieve pyrimidine derivatives (7) via one-pot triflic acid (TfOH)-catalyzed condensation of aldehyde and ketone in the presence of ammonium acetate in DMF. The desired pyrimidine derivatives were obtained after heating at 110 C for 20 h to achieve (7) in 83% yield [138] (Scheme 2).…”

Section: One-pot Methodsmentioning

confidence: 99%

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Farooq

Ngaini

2021

Journal of Heterocyclic Chem

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Chalcone-derived pyrimidine is a well-known heterocyclic compound that is commonly present in ribonucleic acid (RNA) and deoxyribonucleic acid (DNA) bio-isosteres. Pyrimidine derivatives are effective in both the electronic industry and drug industries. This review highlights the synthesis of pyrimidines, namely mono-pyrimidine, bis-pyrimidine, fused pyrimidine, symmetric, and asymmetric pyrimidine via one-pot and two-pot methods. The one-pot method is the direct reaction of amino derivatives with aldehydes and acetophenones, whereas the two-pot method is frequently reported for the synthesis of chalcone before the cyclization to a pyrimidine. This review is important in organic synthesis, particularly in the heterocyclic field, regarding pyrimidines and their significance in therapeutic and electronic industries.

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An efficient route for annulation of pyrimidines to steroids and non-steroids via a base catalyzed one-pot three component reaction

Cited by 11 publications

References 17 publications

Beyond Pseudo‐natural Products: Sequential Ugi/Pictet‐Spengler Reactions Leading to Steroidal Pyrazinoisoquinolines That Trigger Caspase‐Independent Death in HepG2 Cells

Beyond Pseudo‐natural Products: Sequential Ugi/Pictet‐Spengler Reactions Leading to Steroidal Pyrazinoisoquinolines That Trigger Caspase‐Independent Death in HepG2 Cells

Steroidal Pyrimidines and Dihydrotriazines as Novel Classes of Anticancer Agents against Hormone-Dependent Breast Cancer Cells

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

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