A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

Reddy, K. Sridhar; Rao, B. Venkateswara

doi:10.1016/j.tetasy.2011.01.021

Cited by 14 publications

(5 citation statements)

References 34 publications

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“…As it can be seen in Figure S1 as well as in Figure 2C, the dominant ion in mass spectra of the stressed samples, besides anisomycin (m/z 266), is the ion with m/z value 224. This compound was previously identified as deacetylanisomycin (Reddy, Rao, 2011;Tolić et al, 2015). Mass and MS/MS spectra of deacetylanisomycin are presented in Figure 3.…”

Section: Degradation Behavior Of Anisomycinmentioning

confidence: 92%

Development and validation of a stability-indicating LC-UV and LC-MS/MS methods for quantitative analysis of anisomycin and identification of degradation products

Tolić¹,

Grujić

Laušević

2018

Braz. J. Pharm. Sci.

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Multifunctional drug anisomycin was subjected to forced degradation in accordance with International Conference on Harmonisation (ICH) guidelines for the first time. The drug was exposed to the recommended stress conditions of hydrolysis (acidic, alkaline and neutral), oxidation, thermal stress and photolysis, in order to investigate its stability. Optimized LC-MS/MS method was validated as recommended by ICH Q2(R1) guideline with respect to the specificity, accuracy, precision, limits of detection and quantitation, linearity and robustness. Anisomycin exhibited high instability under alkaline and thermal (neutral hydrolysis) conditions. It showed moderate stability under acidic, neutral, oxidative, thermal (acidic hydrolysis) and photolytic conditions, with the lowest degradation level observed in the case of light and oxidation stress. Formation of the same degradation product, identified as deacetylanisomycin, was observed under all applied stress conditions.

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Section: Degradation Behavior Of Anisomycinmentioning

confidence: 92%

Development and validation of a stability-indicating LC-UV and LC-MS/MS methods for quantitative analysis of anisomycin and identification of degradation products

Tolić¹,

Grujić

Laušević

2018

Braz. J. Pharm. Sci.

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“…3-chlorobenzoperoxoic acid was used for the oxidation reaction to obtain compounds 1 and 7 with a 56% and 40% yield, respectively, from the last two steps. Aromatization and oxidation reactions were achieved in a one-pot reaction [19][20][21][22] without isolation of the selenide compounds 11a-d.…”

Section: Synthesis Of Hexahydrocannabinol and Its Analogsmentioning

confidence: 99%

Saturated Cannabinoids: Update on Synthesis Strategies and Biological Studies of These Emerging Cannabinoid Analogs

Docampo-Palacios,

Ramirez,

Tesfatsion

et al. 2023

Molecules

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Natural and non-natural hexahydrocannabinols (HHC) were first described in 1940 by Adam and in late 2021 arose on the drug market in the United States and in some European countries. A background on the discovery, synthesis, and pharmacology studies of hydrogenated and saturated cannabinoids is described. This is harmonized with a summary and comparison of the cannabinoid receptor affinities of various classical, hybrid, and non-classical saturated cannabinoids. A discussion of structure–activity relationships with the four different pharmacophores found in the cannabinoid scaffold is added to this review. According to laboratory studies in vitro, and in several animal species in vivo, HHC is reported to have broadly similar effects to Δ9-tetrahydrocannabinol (Δ9-THC), the main psychoactive substance in cannabis, as demonstrated both in vitro and in several animal species in vivo. However, the effects of HHC treatment have not been studied in humans, and thus a biological profile has not been established.

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“…In 2011, B. V. Rao and co-workers reported the synthesis of 227, the C2 epimer of (+)-deacetylanisomycin, starting from 1,2:3,4-di-O-isopropylidene-D-mannitol (234), which was synthesized from D-mannitol. 54 The alcohol 234 was mesylated using MsCl and Et 3 N to give the mesylate intermediate 254, which was further treated with NaN 3 and DMF to deliver the azide 255 in 83% yield. The reduction of azide functionality with Pd/C, MeOH gave a free amine 256, which on protection with CbzCl and Na 2 CO 3 afforded a secondary amine 257 in 81% yield.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Studies Towards the Synthesis of (+)- and (–)-Anisomycin and Their Analogues

Ajay

Shaw

2017

Synthesis

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Anisomycin shows potent biological activity and it has attracted much attention since its isolation in 1954, with around 13 total syntheses and 20 formal syntheses, and also two reports concerning analogues of anisomycin, reported to date. The present review highlights all of these synthetic approaches (around 35) to the total or formal synthesis of anisomycin along with its isomers and analogues.1 Introduction2 Isolation and Therapeutic Importance3 Total Synthesis of (+)-, (–)-, and (±)-Anisomycins and Their Analogues4 Formal Synthesis of (+)- and (–)-Anisomycins and Their Analogues5 Conclusion

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A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

Cited by 14 publications

References 34 publications

Development and validation of a stability-indicating LC-UV and LC-MS/MS methods for quantitative analysis of anisomycin and identification of degradation products

Development and validation of a stability-indicating LC-UV and LC-MS/MS methods for quantitative analysis of anisomycin and identification of degradation products

Saturated Cannabinoids: Update on Synthesis Strategies and Biological Studies of These Emerging Cannabinoid Analogs

Studies Towards the Synthesis of (+)- and (–)-Anisomycin and Their Analogues

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