Synthesis and analgesic activity of new α-truxillic acid derivatives with monoterpenoid fragments

Соколова, А. С.; Павлова, А. В.; Комарова, Н. И.; Ardashov, Oleg V.; Shernyukov, Аndrey V.; Gatilov, Yuriy V.; Yarovaya, Оlga I.; Толстикова, Т. Г.; Salakhutdinov, N. F.

doi:10.1007/s00044-016-1593-z

Cited by 19 publications

(13 citation statements)

References 29 publications

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“…We highlight that the 2 phytochemicals, Onosmone and Truxillic acid, that have no similarity with any of the FDA approved drugs are among the isolated nodes in the similarity network (Supplementary Figure S1b ). Based on plant-phytochemical associations in our database, Onosmone and Truxillic acid are phytochemicals of Indian medicinal plants, Onosma echioides and Erythroxylum coca , respectively, and a survey of the literature shows that these phytochemicals are under active investigation for their therapeutic uses 99 – 103 . We also highlight that none of the 14 most-druggable phytochemicals are captured by Phytochemica 11 database while 6 of the 14 phytochemicals are captured by Nutrichem 9 , 10 database.…”

Section: Resultsmentioning

confidence: 99%

IMPPAT: A curated database of Indian Medicinal Plants, Phytochemistry And Therapeutics

Mohanraj

Karthikeyan

Vivek-Ananth

et al. 2018

Sci Rep

435

203

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Phytochemicals of medicinal plants encompass a diverse chemical space for drug discovery. India is rich with a flora of indigenous medicinal plants that have been used for centuries in traditional Indian medicine to treat human maladies. A comprehensive online database on the phytochemistry of Indian medicinal plants will enable computational approaches towards natural product based drug discovery. In this direction, we present, IMPPAT, a manually curated database of 1742 Indian Medicinal Plants, 9596 Phytochemicals, And 1124 Therapeutic uses spanning 27074 plant-phytochemical associations and 11514 plant-therapeutic associations. Notably, the curation effort led to a non-redundant in silico library of 9596 phytochemicals with standard chemical identifiers and structure information. Using cheminformatic approaches, we have computed the physicochemical, ADMET (absorption, distribution, metabolism, excretion, toxicity) and drug-likeliness properties of the IMPPAT phytochemicals. We show that the stereochemical complexity and shape complexity of IMPPAT phytochemicals differ from libraries of commercial compounds or diversity-oriented synthesis compounds while being similar to other libraries of natural products. Within IMPPAT, we have filtered a subset of 960 potential druggable phytochemicals, of which majority have no significant similarity to existing FDA approved drugs, and thus, rendering them as good candidates for prospective drugs. IMPPAT database is openly accessible at: https://cb.imsc.res.in/imppat.

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Section: Resultsmentioning

confidence: 99%

IMPPAT: A curated database of Indian Medicinal Plants, Phytochemistry And Therapeutics

Mohanraj

Karthikeyan

Vivek-Ananth

et al. 2018

Sci Rep

435

203

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“…2‐Chloro‐ N ‐[(1 R ,2 R ,4 R )‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐yl]acetamide ( 32 ). To a mixture of amine 31 (0.012 mol), which has been synthesized by a procedure described previously, and Et 3 N (0.012 mol) in 20 ml dry CH 2 Cl 2 at 15 – 18 °C in an Ar atmosphere was added chloroacetyl chloride (0.017 mol), and the mixture was stirred at room temperature for 24 h. The organic layers were washed with brine and extracted with CHCl 3 . The combined organic phase was dried over anhydrous Na 2 SO 4 and the solvent was removed.…”

Section: Methodsmentioning

confidence: 99%

Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor

Соколова

Yarovaya

Бормотов

et al. 2018

Chemistry & Biodiversity

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A series of the bornyl ester/amide derivatives with N-containing heterocycles were designed and synthesized as vaccinia virus (VV) inhibitors. Bioassay results showed that among the designed compounds, derivatives 6, 13, 14, 34, 36 and 37 showed the best inhibitory activity against VV with the IC values of 12.9, 17.9, 3.4, 2.5, 12.5 and 7.5 μm, respectively, and good cytotoxicity. The primary structure-activity relationship (SAR) study suggested that the combination of a saturated N-heterocycle, such as morpholine or 4-methylpiperidine, and a 1,7,7-trimethylbicyclo[2.2.1]heptane scaffold was favorable for antiviral activity.

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“…Sokolova et al [ 97 ] presented the efficient synthesis of α -truxillic acid derivatives containing a monoterpenoid fragment. The authors used natural terpene, (+)-camphor, as a starting monoterpenoid because of its high biological activity and commercial availability.…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

“…Another work showing a new (–)-borneol ester derivative [ 97 ] focuses on the efficient synthesis of bis((1 R ,4 R )-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl) 2,4-diphenylcyclobutane-1,3-dicarboxylate 131 using α -truxillic acid and monoterpenoid bicyclic (–)-borneol as the substrates ( Figure 35 ). The new terpene compound obtained by Sokolova et al exhibits a considerable analgesic activity.…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Zielińska-Błajet

Feder‐Kubis

2020

IJMS

220

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Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

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Synthesis and analgesic activity of new α-truxillic acid derivatives with monoterpenoid fragments

Cited by 19 publications

References 29 publications

IMPPAT: A curated database of Indian Medicinal Plants, Phytochemistry And Therapeutics

IMPPAT: A curated database of Indian Medicinal Plants, Phytochemistry And Therapeutics

Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

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