- New xanthine oxidase inhibitors from the fruiting bodies of Tyromyces fissilis
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Excessive uric acid production, which causes gout and hyperuricemia, can be blocked by inhibiting xanthine oxidase (XO). However, some agents to block on XO often cause side effects, thereby necessitating the identification of new inhibitors. During the s
- Mitomo, Shunsuke,Hirota, Mitsuru,Fujita, Tomoyuki
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- Phenolic Lipids Derived from Cashew Nut Shell Liquid to Treat Metabolic Diseases
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Metabolic diseases are increasing at staggering rates globally. The peroxisome proliferator-activated receptors (PPARα/γ/δ) are fatty acid sensors that help mitigate imbalances between energy uptake and utilization. Herein, we report compounds derived from phenolic lipids present in cashew nut shell liquid (CNSL), an abundant waste byproduct, in an effort to create effective, accessible, and sustainable drugs. Derivatives of anacardic acid and cardanol were tested for PPAR activity in HEK293 cell co-transfection assays, primary hepatocytes, and 3T3-L1 adipocytes. In vivo studies using PPAR-expressing zebrafish embryos identified CNSL derivatives with varying tissue-specific activities. LDT409 (23) is an analogue of cardanol with partial agonist activity for PPARα and PPARγ. Pharmacokinetic profiling showed that 23 is orally bioavailable with a half-life of 4 h in mice. CNSL derivatives represent a sustainable source of selective PPAR modulators with balanced intermediate affinities (EC50 ~100 nM to 10 μM) that provide distinct and favorable gene activation profiles for the treatment of diabetes and obesity.
- Sahin, Cigdem,Magomedova, Lilia,Ferreira, Thais A. M.,Liu, Jiabao,Tiefenbach, Jens,Alves, Priscilla S.,Queiroz, Fellipe J. G.,Oliveira, Andressa S. De,Bhattacharyya, Mousumi,Grouleff, Julie,Nogueira, Patrícia C. N.,Silveira, Edilberto R.,Moreira, Daniel C.,Leite, José Roberto Souza De Almeida,Brand, Guilherme D.,Uehling, David,Poda, Gennady,Krause, Henry,Cummins, Carolyn L.,Romeiro, Luiz A. S.
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p. 1961 - 1978
(2022/02/14)
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- Synthesis and antidiabetic evaluation of 5-(2-methoxy-6-pentadecylbenzylidene)-3-alkyl/aryl substituted thiazolidine-2, 4-dione derivatives
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Compounds containing the thiazolidinedione moiety have been found to exhibit various pharmacological and biological activities viz., COX-2 inhibitor, antihyperglycemic, anti-inflammatory, antioxidant, cytotoxic, antimicrobial etc. The present paper descri
- Reddy, M. Upendar,Reddy, M.C. Somasekhara
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p. 1231 - 1236
(2018/05/29)
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- Synthesis, characterization and antimicrobial evaluation of (E)-N'-[(1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl]-methylene)benzohydrazide derivatives
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Anacardic acid (pentadecyl salicylic acid) is a phenolic constituent present in cashew nut shell liquid (Anacardium occidentale L.) and exhibits antimicrobial properties. The present paper describes the synthesis, characterization and antimicrobial evaluation of hydrazone derivatives of anacardic acid (9a-l) linked with 1,2,3-triazole ring. All the newly synthesized compounds were determined by 1H NMR, mass and IR spectroscopy. Compounds 9d, 9e, 9h, 9i and 9j exhibited strong antifungal activity against the tested fungal strains viz., A. Niger and C. albicans.
- Rambabu,Dubey,Ram,Balram
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p. 175 - 180
(2016/01/20)
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- Synthesis of azabicyclo[3.1.0]amine analogues of anacardic acid as potent antibacterial agents
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Azabicyclo[3.1.0]amine analogues of anacardic acid (16a, 16b, 18a, 18b, 19 and 19b) were synthesized from anacardic acid and tested for their antibacterial activity against Gram positive and Gram negative bacteria. Most of the compounds are having potency at par with ampicillin and inferior with other standard drugs.
- Vempati, Ravi Kumar,Reddy,Alapati, Srinivasa Rao,Dubey
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p. 986 - 994
(2013/06/26)
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- Synthesis and antibacterial activity of sulfonamide derivatives of anacardicacid mixture isolated from a natural product Cashew Nut Shell Liquid (CNSL)
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Abstract: Synthesis and antibacterial activity of some novel sulfonamide derivatives of anacardic acid were (8a-8l) prepared from commercially available anacardic acid mixture (1a-d) isolated from a natural product Cashew Nut Shell Liquid (CNSL).Compounds (8a-8l) were tested for Gram positive and Gram negative bacterial cultures. Most of the compounds were showed active compared with standard drug ampicilline.
- Reddy, N. Subhakara,Rao, A. Srinivas,Chari, M. Adharvana,Kumar, V. Ravi,Jyothy,Himabindu
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experimental part
p. 287 - 293
(2012/07/31)
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- Synthesis and antibacterial activity of anacardic acid derivatives
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New anacardic acid derivatives (6a -6u) were prepared from commercially available anacardic acid and tested for Gram positive and Gram negative activities. Most compounds were found to be active compared to ampicillin.
- Nallamillia, Subhakara Reddy,Kumara, V. Ravi,Himabindub,Rama,Aalapati, Srinivas Rao
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p. 626 - 632
(2012/05/05)
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- Modulators (inhibitors/ activators) of histone acetyltransferases
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Disclosed are compounds of the formulae: and method of using the compounds to treat cancer, AIDS, HIV infection, and asthma.
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Page/Page column 2
(2008/06/13)
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- COMPOUNDS CAPABLE OF ABSORBING ULTRAVIOLET RADIATION, COMPOSITIONS CONTAINING THEM AND PROCESSES FOR THEIR PREPARATION
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The molecules capable of absorbing ultraviolet radiation from the cashew nut shell liquid changes are the object of the present invention; it is also described the compositions responsible for protecting the surfaces and chemical processes for the referred molecules production.
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Page/Page column 30
(2008/06/13)
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- Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors
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We have synthesised a series of 2-[[2-alkoxy-6-pentadecylphenyl)methyl]thio]-1H-benzimidazoles/benzothiazoles and benzoxazoles from anacardic acid and investigated their ability to inhibit human cyclooxygenase-2 enzyme (COX-2). The active compounds were s
- Paramashivappa,Phani Kumar,Subba Rao,Srinivasa Rao
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p. 657 - 660
(2007/10/03)
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- Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition
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Anacardic acid (6-pentadecylsalicylic acid), a major component of cashew nut shell liquid, consists of a heterogeneous mixture of monoenes, dienes, and trienes. The enes mixture of anacardic acid was hydrogenated to a saturated compound. Using saturated a
- Paramashivappa,Phani Kumar,Subba Rao,Srinivasa Rao
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p. 7709 - 7713
(2007/10/03)
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- Synthesis and evaluation of a new class of nifedipine analogs with T-type calcium channel blocking activity
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We have synthesized a novel series of 18 dialkyl 1,4-dihydro-4-(2′alkoxy-6′-pentadecylphenyl)-2,6-dimethyl-3,5 pyddine dicarboxylates from anacardic acid, a natural compound found in cashew nut shells, and investigated their blocking action on L- and T-type calcium channels transiently expressed in tSA-201 cells. The IC50 values for L-type calcium channel block obtained with the series ranged from 1 to ~40 μM, with higher affinities being favored by increasing the size of the alkoxy group on the 4-phenyl ring and ester substituent in the 3,5 positions. A detailed analysis of the strongest L-type channel blocker of the series (PPK-12) revealed that block was poorly reversible and mediated an apparent speeding of the time course of inactivation. Moreover, in the presence of PPK-12, the midpoint of the steady state inactivation curve was shifted by 20 mV toward more hyperpolarized potentials, resulting in an increase in blocking efficacy at more depolarized holding potentials. Surprisingly, PPK-12 blocked T- and L-type calcium channels with similar affinities. One of the weakest L-type channel inhibitors (PPK-5) exhibited a T-type channel affinity that was similar to that seen with PPK-12, resulting in a 40-fold selectivity of PPK-5 for T- over L-type channels. Thus, dialkyl 1,4-dihydro-4-(2′alkoxy-6′-pentadecylphenyl)-2,6-dimethyl-3,5 pyridine dicarboxylates may serve as excellent candidates for the development of T-type calcium-channel specific blockers.
- Phani Kumar,Stotz, Stephanie C.,Paramashivappa,Beedle, Aaron M.,Zamponi, Gerald W.,Srinivasa Rao
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p. 649 - 658
(2007/10/03)
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- Synthesis of Anacardic Acids
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The anacardic acids 1-11, isolated from various plants, were synthesized by a new general method.Reaction of the methyl alkynoates 12-18 with 1-methoxy-1,4-cyclohexadiene at 200 deg C afforded directly the methyl 2-methoxybenzoates 19-25 with long chain substituents in 6-position in 74-85percent yield.The dienophiles 12-16 were prepared by pyrolysis of the corresponding acylphosphoranes 26-30, the dienophiles 17 and 18 by methoxycarbonylation of the corresponding alkynes 31 and 32 via the hydroxy esters 33 and 34.Demethylation of 19-23 with AlI3 gave the methyl salicylates 35-39 which could be hydrolized to the anacardic acids 1-4 and 7.Hydrolysis of 24 and 25 provided the hydroxy acids 40 and 41, which were converted by treatment with CBr4/PPh3 into the acids 42 and 43 bearing bromoalkyl side chains.These were transformed into 44-47 by reaction with 1-hexynyllithium and 1-octynyllithium.Stereoselective hydrogenation of 44-47 gave 48-51 with (Z)-alkene side chains.In a similar approach 42 was converted into 52 and then into 53, which gave upon treatment with 1-pentynylmagnesium bromide or 1-heptynylmagnesium bromide the acids 54 and 55 with alkadiyne side chains.Stereoselective hydrogenation provided 56 and 57 with (Z,Z)-alkadiene side chains.The 2-methoxy group in 48-51, 56, 57 was demethylated by treatment with AlI3 to give the anacardic acids 5, 6, 8-11. - Keywords: Anacardic acids; Benzoates, methyl 6-alkyl-2-methoxy-; 2-Alkynoates, methyl; Aluminium triiodide, demethylation by treatment with
- Zehnter, Reinhard,Gerlach, Hans
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p. 2209 - 2220
(2007/10/03)
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- Long Chain Alkyl Phenols from the Liverwort Schistochila Appendiculata
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3-Undecyl phenol, 6-undecyl salicylic acid and potassium 6-undecyl salicylate were isolated from the New Zealand liverwort Schistochila appendiculata. 3-Tridecyl and 3-pentadecyl phenol, 6-tridecyl and 6-pentadecyl salicylic acid, potassium 6-tridecyl and 6-pentadecyl salicylate and 6-undecyl catechol were also detected in the same species.The chemical constitution of S. appendiculata is quite similar to that of the brown algae Caulocystis species, and of the higher plants Ginkgo biloba and some of the Anacardia species.The allergic reaction brought on by S. appendiculata might be due to the presence of these phenolic compounds.Key Word Index - Schistochila appendiculata; Jungermanniales; Hepaticae; long chain alkyl phenols; 3-undecyl, 3-tridecyl, 3-pentadecyl phenols; 6-undecyl, 6-tridecyl, 6-pentadecyl salicylic acids; potassium 6-undecyl, 6-tridecyl, 6-pentadecyl salicylates; 6-undecyl catechol; allergy; chemosystematics.
- Asakawa, Yoshinori,Masuya, Toru,Tori, Motoo,Campbell, Ella O.
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p. 735 - 738
(2007/10/02)
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- Long-chain Phenols. Part 18. Conversion of Anacardic Acid into Urushiol
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(15:0)-Anacardic acid (6-pentadecylsalicylic acid), prepared by reduction of unsaturated anacardic acid from Anacardium occidentale, has been converted into anacardic alcohol (6-pentadecylsalicylic alcohol) and thence by oxidation at carbon into anacardaldehyde.Phenolic oxidation of anacardic alcohol led to 8-pentadecyl-1-oxaspiroocta-5,7-dien-4-one, itself readily convertible photochemically, but less so thermally, into anacardaldehyde.Reaction of thionyl chloride with anacardic acid led mainly to the anhydride, which by hydride reduction gave anacardaldehyde less satisfactorily.Dakin oxidation of anacardaldehyde furnished (15:0)-urushiol (3-pentadecylcatechol) identical chemically and from argentation t.l.c. with the hydrogenated natural product from Rhus vernicifera. (15:0)-Cardanol (3-pentadecylphenol) has been detected in hydrogenated urushiol.The composition of the unsaturated constituents of urushiol from Rhus vernicifera and Rhus toxicodendron and its mode of formation have been discussed.An improved synthesis of (15:0)-urushiol has been devised based on an organo-lithium route.Aromatic methyl ether and ester formation in this series is greatly facilitated by phase-transfer catalysis.
- Kiong, Lam Soot,Tyman, John H. P.
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p. 1942 - 1952
(2007/10/02)
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