Study of structure-activity relationships in a series of alkaloids ofAconitum zeravschanicum and their analogs

Salimov, B. T.; Kuzibaeva, Zh. Kh.; Dihakhangirov, F. N.

doi:10.1007/bf01372341

Cited by 13 publications

(14 citation statements)

References 5 publications

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“…Toxicity and antiarrhythmic activity of heteratisine and other diterpenoid alkaloids were studied as functions of their molecular structures. 38 The C 19 -diterpenoid alkaloid lappaconitine isolated from Aconitum sinomontanum possesses analgesic and antiinflammatory properties in vivo and inhibits neuronal activity in brain slices. Ameri recently investigated the effect of three structurally related diterpenoid alkaloids, lappaconitine, N-deacetyllappaconitine and lappaconidine on neuronal activity in rat hippocampal slices.…”

Section: Pharmacologymentioning

confidence: 99%

Diterpenoid and steroidal alkaloids

Atta-ur-Rahman¹,

Choudhary²

1999

Nat. Prod. Rep.

176

188

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Section: Pharmacologymentioning

confidence: 99%

Diterpenoid and steroidal alkaloids

Atta-ur-Rahman¹,

Choudhary²

1999

Nat. Prod. Rep.

176

188

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“…However, the acylation of all hydroxy groups, including position 13 (17), leads to the disappearance of toxicity. The removal of all ester groups from the aconitine molecule also results in the formation of the nontoxic compound, viz., aconine (18). Based on the experimental data and the analysis of the literature, it can be concluded that the hydroxy group at C(13) and the benzoyl group or another aromatic acid group at O (14) are required for the arrhyth mogenic properties of C 19 DTA.…”

Section: Methodsmentioning

confidence: 96%

“…Taking into account the structure-activity relationship, it is reasonable to design efficient antiarrhythmic agents based on available alka loids isolated from plants of the genus Delphinium be cause these plants are easy to culture. (17) 150.0 Aconine (18) 200.0 14 Benzoylaconine 16.0 * Studies were carried out in mice, the agent was adminis tered intravenously.…”

Section: Methodsmentioning

confidence: 99%

“…The reduction of a mixture of atisine and isoatisine (with NaBH 4 in EtOH) gave the only product, viz., dihydroatisine (14) (see Scheme 3), which proved to be an efficient antiarrhythmic agent. 18 The alkaline solution was neutralized. The pure hetera tisine was extracted with chloroform and was used for the synthesis of benzoylheteratisine (5).…”

Section: Methodsmentioning

confidence: 99%

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Antiarrhythmic agents based on diterpenoid alkaloids

Yunusov

2011

Russ Chem Bull

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Diterpenoid alkaloids comprise a large group of natural compounds produced by the plants of the genera Aconitum and Delphinium. Some of these compounds were found to manifest valuable pharmacological properties, including the unique antiarrhythmic activity. Allapinine (derived from the alkaloid lappaconitine) was approved as a drug. The investigation of the structure-activity relationship revealed structural elements responsible for the arrhythmogenic and antiarrhythmic properties.

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“…45b Like lappaconitine, some can counter the arrhythmic effects of aconitine poisoning and this has prevented death in animals poisoned with lethal doses of aconitine. 51,52 So far, only the work of Wiesner has resulted in the successful total syntheses of several C 19 -diterpenoid alkaloids possessing a variety of skeletons.…”

Section: Diterpenoid Alkaloidsmentioning

confidence: 99%

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

Cherney

Baran

2011

Israel Journal of Chemistry

101

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Terpenes and alkaloids are ever-growing classes of natural products that provide new molecular structures which inspire chemists and possess a broad range of biological activity. Terpenoid-alkaloids originate from the same prenyl units that construct terpene skeletons. However, during biosynthesis, a nitrogen atom (or atoms) is introduced in the form of β-aminoethanol, ethylamine, or methylamine. Nitrogen incorporation can occur either before, during, or after the cyclase phase. The outcome of this unique biosynthesis is the formation of natural products containing unprecedented structures. These complex structural motifs expose current limitations in organic chemistry, thus providing opportunities for invention. This review focuses on total syntheses of terpenoid-alkaloids and unique issues presented by this class of natural products. More specifically, it examines how these syntheses relate to the way terpenoid-alkaloids are made in Nature. Developments in chemistry that have facilitated these syntheses are emphasized, as well as chemical technology needed to conquer those that evade synthesis.

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Study of structure-activity relationships in a series of alkaloids ofAconitum zeravschanicum and their analogs

Cited by 13 publications

References 5 publications

Diterpenoid and steroidal alkaloids

Diterpenoid and steroidal alkaloids

Antiarrhythmic agents based on diterpenoid alkaloids

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

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