79688-40-7Relevant academic research and scientific papers
Synthesis, characterization and antimicrobial evaluation of (E)-N'-[(1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl]-methylene)benzohydrazide derivatives
Rambabu,Dubey,Ram,Balram
, p. 175 - 180 (2016)
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.
Synthesis and antidiabetic evaluation of 5-(2-methoxy-6-pentadecylbenzylidene)-3-alkyl/aryl substituted thiazolidine-2, 4-dione derivatives
Reddy, M. Upendar,Reddy, M.C. Somasekhara
, p. 1231 - 1236 (2018/05/29)
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
Synthesis of azabicyclo[3.1.0]amine analogues of anacardic acid as potent antibacterial agents
Vempati, Ravi Kumar,Reddy,Alapati, Srinivasa Rao,Dubey
, p. 986 - 994 (2013/06/26)
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.
Synthesis and antibacterial activity of sulfonamide derivatives of anacardicacid mixture isolated from a natural product Cashew Nut Shell Liquid (CNSL)
Reddy, N. Subhakara,Rao, A. Srinivas,Chari, M. Adharvana,Kumar, V. Ravi,Jyothy,Himabindu
experimental part, p. 287 - 293 (2012/07/31)
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.
Synthesis and antibacterial activity of anacardic acid derivatives
Nallamillia, Subhakara Reddy,Kumara, V. Ravi,Himabindub,Rama,Aalapati, Srinivas Rao
, p. 626 - 632 (2012/05/05)
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.
Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors
Paramashivappa,Phani Kumar,Subba Rao,Srinivasa Rao
, p. 657 - 660 (2007/10/03)
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
Synthesis and evaluation of a new class of nifedipine analogs with T-type calcium channel blocking activity
Phani Kumar,Stotz, Stephanie C.,Paramashivappa,Beedle, Aaron M.,Zamponi, Gerald W.,Srinivasa Rao
, p. 649 - 658 (2007/10/03)
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.
Long-chain Phenols. Part 18. Conversion of Anacardic Acid into Urushiol
Kiong, Lam Soot,Tyman, John H. P.
, p. 1942 - 1952 (2007/10/02)
(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.
