Diastereoselective Synthesis of Functionalized Angularly‐Fused Tetracycles <i>via</i> an Organocatalytic Quadruple Reaction Sequence

Chang, Fu Jie; Gurubrahamam, Ramani; Chen, Kwunmin

doi:10.1002/adsc.201700023

Cited by 8 publications

(5 citation statements)

References 124 publications

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“…It is known that Knoevenagel condensation reactions yields are influenced by the stereochemistry of the used aldehyde. Compounds 1, 3, 4, 5, 6, 10 have been synthesized earlier under different experimental conditions [38,39,40,41,42,43,44,45,46,47,48,49,50,51]. We used a different synthetic technique and the structures of the known compounds were verified according to the given in the literature spectral data, elemental analysis, or mps.…”

Section: Resultsmentioning

confidence: 99%

“…Yield: 47%; m.p.165-167 °C; IR (Nujol) (cm −1 ): 1740, 1700, 1580; 1 H-NMR (300 MHz, CDCl 3 ): δ (ppm) 6.48–6.99 (m, 2H, C H =C H ), 7.33–8.10 (br, 9H, aromatics), 9.31 (d, 1H, J = 8.4 Hz); 13 C-NMR (75 MHz, CDCl 3 ): 125.5, 125.8, 126.4, 126.5, 127.2, 127.3, 127.6, 127.8, 128.4, 128.5, 129.8, 137.0, 138.1, 138.2, 143.2, 144.0, 192.7, 192.8; Anal. C, H. Calcd %: (C 18 H 12 O 2 ) C: 83.06, H: 4.65, Found %: C: 83, H: 4.60 [45,46,47].…”

Section: Methodsmentioning

confidence: 99%

“…Some of these derivatives, compounds 1 , 3 , 4 , 5 , 6 , 10 are referred in the literature as tyrosinase kinase inhibitors, in the treatment of schistosomiasis whereas 3 as a urease inhibitor. However their synthesis follow a different route from the described herein procedure [38,39,40,41,42,43,44,45,46,47,48,49,50,51].…”

Section: Introductionmentioning

confidence: 99%

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2-Arylidene-1-indandiones as Pleiotropic Agents with Antioxidant and Inhibitory Enzymes Activities

2019

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Indandiones are a relatively new group of compounds presenting a wide range of biological activities. The synthesis of these compounds was performed via a Knoevenagel reaction between an aldehyde and 1,3-indandione and were obtained with a yield up to 54%. IR, 1H-Nucleic Magnetic Resonance (NMR), 13C-NMR, LC/MS ESI+ and elemental analysis were used for the confirmation of the structures of the novel derivatives. Lipophilicity values of compounds were calculated theoretically and experimentally by reversed chromatography method as values RM. The novel derivatives were studied through in vitro and in vivo experiments for their activity as anti-inflammatory and antioxidant agents and as inhibitors of lipoxygenase, trypsin, and thrombin. The inhibition of the carrageenin-induced paw edema (CPE) was also determined for representative structures. In the above series of experiments, we find that all the compounds showed moderate to satisfying interaction with the stable DPPH free radical in relation to the concentration and the time 2-arylidene-1-indandione (10) was the strongest. We observed moderate or very low antioxidant activities for selected compounds in the decolorization assay with ABTS+•. Most of the compounds showed high anti-lipid peroxidation of linoleic acid induced by AAPH.2-arylidene-1-indandione (7) showed a strongly inhibited soybean LOX. Only 2-arylidene-1-indandione (3) showed moderate scavenging activity of superoxide anion, whereas 2-arylidene-1-indandione (8) and 2-arylidene-1-indandione (9) showed very strong inhibition on proteolysis. 2-arylidene-1-indandione (8) highly inhibited serine protease thrombin. 2-arylidene-1-indandiones (7, 8 and 9) can be used as lead multifunctional molecules. The compounds were active for the inhibition of the CPE (30–57%) with 2-arylidene-1-indandione (1) being the most potent (57%). According to the predicted results a great number of the derivatives can cross the Blood–Brain Barrier (BBB), act in CNS and easily transported, diffused, and absorbed. Efforts are conducted a) to correlate quantitatively the in vitro/in vivo results with the most important physicochemical properties of the structural components of the molecules and b) to clarify the correlation of actions among them to propose a possible mechanism of action. Hydration energy as EHYDR and highest occupied molecular orbital (HOMO) better describe their antioxidant profile whereas the lipophilicity as RM values governs the in vivo anti-inflammatory activity. Docking studies are performed and showed that soybean LOX oxidation was prevented by blocking into the hydrophobic domain the substrates to the active site.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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2-Arylidene-1-indandiones as Pleiotropic Agents with Antioxidant and Inhibitory Enzymes Activities

2019

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“…Spectral data (NMR, IR) are consistent with published data. 43 General Procedure B (Corey−Chaykovsky Cyclopropanation). To a stirred suspension of NaH (60% in oil) in dry DMF or DMSO trimethylsulfoxonium iodide was added in a single portion under argon atmosphere at room temperature.…”

Section: ■ Conclusionmentioning

confidence: 99%

Lewis Acid Triggered Vinylcyclopropane–Cyclopentene Rearrangement

et al. 2017

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We report a mild Lewis acid induced isomerization of donor-acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51-99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor-acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.

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“…Impor-tantly, we found that the properties of organobases' conjugated acid were critical in directing the reaction pathway for further 1,4-or 1,2-addition. These prominent results encouraged us to keep on studying the organobase-controlled reactions of allylidene indandiones [6] with suitable substrates.…”

mentioning

confidence: 99%

Diversity‐Oriented Synthesis of Spiro‐ and 3‐Methylene‐hydroquinoline‐Indandiones via an Organobase‐Controlled Cascade Strategy

et al. 2023

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The catalyst‐controlled diversity‐oriented synthesis of spirohydroquinoline‐indandiones and 3‐methylenehydroquinoline‐indandiones from ortho‐sulfonamidophenyl‐substituted para‐quinone methides and allylidene‐indandiones is reported. The strategies utilized an organobase such as DMAP or TMG to control the reaction pathway chemoselectively, furnishing the corresponding products in 40–99% yields with excellent diastereoselectivities. The mechanistic studies revealed that spirohydroquinoline‐indandione was the kinetic product to afford 3‐methylenehydroquinoline‐indandione in the presence of TMG, which probably involved an unusual base‐initiated 1,3‐nitrogen rearrangement process.

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Diastereoselective Synthesis of Functionalized Angularly‐Fused Tetracycles via an Organocatalytic Quadruple Reaction Sequence

Cited by 8 publications

References 124 publications

2-Arylidene-1-indandiones as Pleiotropic Agents with Antioxidant and Inhibitory Enzymes Activities

2-Arylidene-1-indandiones as Pleiotropic Agents with Antioxidant and Inhibitory Enzymes Activities

Lewis Acid Triggered Vinylcyclopropane–Cyclopentene Rearrangement

Diversity‐Oriented Synthesis of Spiro‐ and 3‐Methylene‐hydroquinoline‐Indandiones via an Organobase‐Controlled Cascade Strategy

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