111-81-9Relevant articles and documents
Comparison of reactivity in the cross metathesis of allyl acetate-derivatives with oleochemical compounds
Behr, Arno,Toepell, Stephanie
, p. 603 - 611 (2015)
The metathesis of unsaturated oleochemicals is an excellent tool for generating α,ω-difunctional substrates, which are useful intermediates for polymer synthesis. This article describes the cross metathesis of allyl acetate and cis-1,4-diacetoxy-2-butene with methyl 10-undecenoate and methyl oleate, which are oleochemical key substrates. Detailed optimizations led to high conversion rates and yields of the desired products under mild reaction conditions by using a low concentration of commercially available homogeneous ruthenium catalysts.
Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids
Narra, Naganna,Kaki, Shiva Shanker,Prasad, Rachapudi Badari Narayana,Misra, Sunil,Dhevendar, Koude,Kontham, Venkateshwarlu,Korlipara, Padmaja V.
, p. 26 - 32 (2017)
The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol-ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were confirmed by spectral data. The antioxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.
Synthesis and biological evaluation of 3,6-dialkylsubstituted-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles
Venepally, Vijayendar,Sirisha,Kumar, C Ganesh,Krishna, E Vamshi,Misra, Sunil,Jala, Ram Chandra Reddy
, (2018)
Abstract: A series of 3,6-dialkyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole (10) analogues were prepared through multistep synthesis and evaluated them for their antimicrobial and cytotoxic activities. Synthesis of target compounds was carried out using undecenoic acid as starting material, which is the renewable product of castor oil. The key step in the synthesis was formation of triazolo [3,4-b][1,3,4]thiadiazole using various free fatty acids in presence of POCl 3. It was observed that the undecenyl based triazolothiadiazole with butyl (6a), hexyl (6b) and lauryl (6f) derivatives exhibited promising antimicrobial activity against the tested strains. Particularly, Compound 6a exhibited the most promising activity with MIC value 3.9 μ g / mL against most of the tested strains. It also showed potent minimum bactericidal concentration activity with MIC value 7.8 μ g / mL against the tested strains. Cytotoxicity data revealed that most of the tested compounds revealed cytotoxic activity, Compounds 6b, 6d, 6f, 6g, 6h and 6i against SKOV3, 6d, 6e, 6f, 6g, 6h, 6i and 6j against MCF-7 and 6c, 6d, 6e,6g, 6h, 6i and6j against B16–F10 cell lines exhibited significant activities with IC 50 values ranged between 13.67 and 18.62 μ M. Interestingly, all the compounds were non toxic against Chinese hamster ovary cell (CHO-K1) normal cell. Graphical Abstract : A series of 3, 6-dialkyl triazolothiadiazole analogues were prepared using undecenoic acid, which is the renewable product of castor oil and evaluated them for their antimicrobial and cytotoxic activities. Few compounds showed good antimicrobial and cytotoxic activities. [Figure not available: see fulltext.].
Anchoring molecular magnets on the Si(100) surface
Condorelli, Guglielmo G.,Motta, Alessandro,Fragala, Ignazio L.,Giannazzo, Filippo,Raineri, Vito,Caneschi, Andrea,Gatteschi, Dante
, p. 4081 - 4084 (2004)
Hydrosilylation by H-terminated silicon of the double bond of methyl 10-undecenoate with formation of a robust Si-C bond is the first step in a three-step procedure (see scheme) for anchoring the single-molecule magnet (SMM) [Mn12O12(OAc)16(H2O)4] (1) on the Si(100) surface.
Chemoenzymatic synthesis of macrocyclic polyamines
Lu, Wei,Sih, Charles J.
, p. 4965 - 4968 (1999)
(±)-Azamacrolides were synthesized via lipase-catalyzed intramolecular cyclization of (±)-hydroxy-azaesters. Further, the size of the macrocyclic lactones formed could be altered by the substituent on the nitrogen atom. This allows one to prepare a combinatorial library of azamacrolides from a small number of hydroxy-azaesters using this biocatalytic approach.
Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
Ahmad, Anis,Ahmad, Aiman,Sudhakar, Raja,Varshney, Himani,Subbarao, Naidu,Ansari, Saba,Rauf, Abdul,Khan, Asad U.
, p. 3412 - 3431 (2017)
In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1H NMR, 13C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8’R)-8’ hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2’R)(2’-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8’R)-8’-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
Factors influencing orientations of covalently-attached and doped aromatic groups in stretched polyethylene films
Wang, Caihua,Xu, Jinqi,Weiss, Richard G.
, p. 7015 - 7025 (2003)
Linear polarizations have been measured for covalently attached and doped 9-anthryl and 1-pyrenyl groups residing in interior sites of stretched polyolefinic films. The influences of polymer crystallinity, the concentration of aromatic groups and the length of the substituents attached to doped molecules or of the tethers to polymer chains of covalently attached species on the degree of polarization have been explored. The results demonstrate the utility of comparing orientational parameters from doped and covalently attached groups in analyzing the factors responsible for stretch-induced orientation. The anthryl and pyrenyl groups prefer to reside in interfacial regions more than amorphous regions even before film stretching, and the specificity of their orientations is determined by the nature of interactions with surrounding polymer chains. The magnitudes of orientation factors are dependent on polymer crystallinity and substituent or tether length, but are independent of aromatic group concentrations as long as they are low. There are significant differences between the orientations of doped and covalently attached groups of the same type due to the inability of the latter to translocate between site types during film stretching. The results, as interpreted in the context of current theories, demonstrate the necessity of crystallite surfaces (i.e., interfacial sites), but not stretching-induced translocation, for selective orientation of aromatic groups along the axis of stretching.
Total Synthesis of Four Isomers of the Proposed Structures of Cryptorigidifoliol K
Reddy, G. Sudhakar,Padhi, Birakishore,Bharath, Yada,Mohapatra, Debendra K.
, p. 6506 - 6509 (2017)
The first asymmetric convergent total synthesis of four isomers of proposed structures of cryptorigidifoliol K (1a, 1b, 1c, and 1d) has been achieved from commercially available starting materials. The key steps in this synthesis involve tandem isomerization followed by a C-O and C-C bond-forming reaction for the construction of trans-2,6-disubstituted dihydropyran, iodolactonization, isomerization of terminal alkene, and cross-metathesis reaction. The large discrepancies in the spectroscopic data (1H NMR) of synthetic cryptorigidifoliol K from the natural product suggest that the structure of the natural cryptorigidifoliol K requires revision.
Stereochemistry of Deconjugative Alkylation of Ester Dienolates. Stereospecific Total Synthesis of the Litsenolides
Kende, Andrew S.,Toder, Bruce H.
, p. 163 - 167 (1982)
Deconjugative protonations, alkylations, and aldol condensations of the dienolates from (Z)-2-alkenoates give the corresponding (E)-3-enoate products, whereas dienolates from (E)-2-enoates give mainly the (Z)-3-enoate products.These generalizations are exploited in stereospecific total syntheses of litsenolides A2, B2, and C2.
Designing and synthesis of novel antimicrobial heterocyclic analogs of fatty acids
Ahmad, Aiman,Ahmad, Anis,Varshney, Himani,Rauf, Abdul,Rehan, Mohd,Subbarao, Naidu,Khan, Asad U.
, p. 887 - 900 (2013)
Novel series of long chain isoxazole derivatives were designed as inhibitors of Cytochrome P450-14DM14a-demethylase from Candida albicans and ribosomal subunit of S12 protein from Escherichia coli. The novel compounds (6-10) were synthesized through 1,3-dipolar cycloaddition of nitrile oxide to long chain alkynoic acid and alkenyl/hydroxyalkenyl esters and tested for their antimicrobial activity by disk diffusion assay and MIC by broth micro dilution method. After predicting the hidden potential and drug-likeness of compounds, ADMET-related descriptors were also calculated to predict pharmacokinetic properties. Molecular docking studies have been performed to evaluate possible mode of action of molecules in active site of receptor. Compounds (9 and 10) showed excellent antimicrobial activity nearly equivalent to the control compounds.
