861552-54-7Relevant articles and documents
An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau
Harig, Marco,Neumann, Beate,Stammler, Hans-Georg,Kuck, Dietmar
, p. 1078 - 1095 (2017/07/25)
This study presents a potential experimental approach to the still elusive topologically nonplanar (K5) parent hydrocarbon, centrohexaquinane (1), by a construction-dismantling (aufbau–abbau) strategy via electron-rich aromatic centropolyindanes. A series of veratrole-based centropolyindanes are synthesized and subjected to ozonolytic degradation. These include the 2,2′-spirobiindanes 30–32, fuso-diindane 33, triptindanes 34–36, tribenzotriquinacene 37, and tetramethoxycentrohexaindane 9. Spirane 30 and propellane 36 are characterized by X-ray structure analysis. Ozonolysis of 32 and 33 gives a keto ester (59) and a dimethyl muconate (60), respectively. Dimethoxytriptindane 34 gives a [3.3.3]propellane-cis,cis-muconate (61) in good yield, the stereochemistry of which is determined by X-ray structure analysis. Tetramethoxytriptindane 35 gives the [3.3.3]propellane-bis-muconate 62 along with a [3.3.3]propellane-dialdehyde-muconate (63). Hexamethoxytriptindane 36 furnishes three products of mainly intra-dimethoxy cleavage, with the [3.3.3]propellane-tris-muconate 64 as the major component. X-ray structure analysis of 64 reveals molecular C3 symmetry and all-cis,cis stereochemistry of the three muconate groups. Hexamethoxytribenzotriquinacene 37 gives the triquinacene-tris-muconate 68, albeit in very low yield. Ozonolysis of tetramethoxycentrohexaindane 9 affords the bis-muconate 10 in moderate yield, along with two further centrohexacyclic products of single-wing degradation.
Synthesis and anticonvulsant activity of 3a,4-dihydro-3H-indeno[1,2-c] pyrazole-2-carboxamide/carbothioamide analogues
Ahsan, Mohamed Jawed,Khalilullah, Habibullah,Stables, James P.,Govindasamy, Jeyabalan
, p. 644 - 650 (2013/05/21)
A series of fourteen 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/ carbothioamide analogues were synthesized and evaluated for anticonvulsant activity according to the Antiepileptic Drug Development Programme (ADD) protocol. Some of the synthesized compounds showed significant activity in minimal clonic seizure model (6 Hz psychomotor seizure test). 3-(4-Fluorophenyl)-N-(4-bromophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c] pyrazole-2-carboxamide (4c) was found to be the most active compound of the series showing 75% (3/4, 0.25-2.0 h) and 50% (2/4, 4.0 h) protection against minimal clonic seizure at 100 mg/kg without any toxicity. 3-(Pyridin-4-yl)-N-(4- chlorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide (4f) showed protection in maximal electroshock (MES) seizure and subcutaneous metrazol (scMET) seizure at 300 mg/kg.
POMA analyses as new efficient bioinformatics' platform to predict and optimise bioactivity of synthesized 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2- carboxamide/carbothioamide analogues
Ahsan, Mohamed Jawed,Govindasamy, Jeyabalan,Khalilullah, Habibullah,Mohan, Govind,Stables, James P.,Pannecouque, Christophe,Clercq, Eric De
, p. 7029 - 7035,7 (2012/12/12)
A series of 43, 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/ carbothioamide analogues (D01-D43) were analysed using Petra, Osiris, Molinspiration and ALOGPS (POMA) to identify pharmacophore, toxicity prediction, lipophilicity and bioactivity. All the compounds were evaluated for anti-HIV activity. 3-(4-Chlorophenyl)-N-(4-fluorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H- indeno[1,2-c]pyrazole-2-carboxamide (D07) was found to be the most active with IC50 > 4.83 μM and CC50 4.83 μM. 3-(4-Fluorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c] pyrazole-2-carbothioamide (D41) was found to be the most active compound against bacterial strains with MIC of 4 μg/ml, comparable to the standard drug ciprofloxacin while 3-(4-methoxyphenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1, 2-c]pyrazole-2-carboxamide (D38) was found to be the most active compound against fungal strains with MIC 2-4 μg/ml, however less active than standard fluconazole. Toxicities prediction by Osiris were well supported and experimentally verified with exception of some compounds. In anticonvulsant screening, 3-(4-fluorophenyl)-N-(4-chlorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H- indeno[1,2-c]pyrazole-2-carboxamide (D09) showed maximum activity showing 100% (4/4, 0.25-0.5 h) and 75% (3/4, 1.0 h) protection against minimal clonic seizure test without any toxicity.
