10340-84-8Relevant articles and documents
Novel tdp1 inhibitors based on adamantane connected with monoterpene moieties via heterocyclic fragments
Chepanova, Arina A.,Dyrkheeva, Nadezhda S.,Ilina, Ekaterina S.,Korchagina, Dina V.,Lavrik, Olga I.,Mozhaitsev, Evgenii S.,Munkuev, Aldar A.,Reynisson, Jóhannes,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Volcho, Konstantin P.,Zakharenko, Alexandra L.,Zakharova, Olga D.
, (2021)
Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising target for anticancer therapy due to its ability to counter the effects topoisomerase 1 (Top1) poison, such as topotecan, thus, decreasing their efficacy. Compounds containing adamantane and monoterpenoid residues connected via 1,2,4-triazole or 1,3,4-thiadiazole linkers were synthesized and tested against Tdp1. All the derivatives exhibited inhibition at low micromolar or nanomolar concentrations with the most potent inhibitors having IC50 values in the 0.35–0.57 μM range. The cytotoxicity was determined in the HeLa, HCT-116 and SW837 cancer cell lines; moderate CC50 (μM) values were seen from the mid-teens to no effect at 100 μM. Furthermore, citral derivative 20c, α-pinene-derived compounds 20f, 20g and 25c, and the citronellic acid derivative 25b were found to have a sensitizing effect in conjunction with topotecan in the HeLa cervical cancer and colon adenocarcinoma HCT-116 cell lines. The ligands are predicted to bind in the catalytic pocket of Tdp1 and have favorable physicochemical properties for further development as a potential adjunct therapy with Top1 poisons.
INSECT PHEROMONES AND THEIR ANALOGUES XXXII. CHIRAL PHEROMONES BASED ON (S)-(+)-3,7-DIMETHYLOCTA-1,6-DIENE. 1. SYNTHESIS OF (4R,8RS)-4,8-DIMETHYLDECANAL
Odinokov, V. N.,Ishmuratov, G. Yu.,Kharisov, R. Ya.,Yakovleva, M. P.,Sultanov, R. M.,et al.
, p. 500 - 502 (1991)
The synthesis of optically active (4R,8RS)-4,8-dimethyldecanal - the aggregation pheromone of the flour beetles Tribolium confusum and T. castaneum - has been effected.The starting compound was the readily available enantiomerically enriched (S)-(+)-3,7-dimethylocta-1,6-diene with an optical purity of ca. 50percent.
Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde
Vydrina,Kravchenko,Yakovleva,Ishmuratova,Ishmuratov, G. Yu.
, p. 461 - 463 (2018)
A stereoselective synthesis of natural (+)-caparratriene was developed starting from commercially available L-menthol and tiglic aldehyde. The key step was a Wittig reaction of the latter with the triphenylphosphorane generated from (R)-(–)-citronellyl bromide. (+)-Caparratriene as a mixture (4:1) of 2E,4E- and 2E,4Z-stereoisomers is a known anticancer agent.
Synthesis of novel chiral ionic liquids and their phase behavior in mixtures with smectic and nematic liquid crystals
Tosoni, Martin,Laschat, Sabine,Baro, Angelika
, p. 2742 - 2749 (2004)
Alkylation of 1-alkyl-1H-imidazoles 2a-f with citronellyl bromide 1b opens access to chiral 1H-imidazolium bromides 3a-f (Scheme 1). A similar strategy yielded the chiral pyridinium ionic liquid 6 (Scheme 2). Dialkylation of 1H-imidazole (7) gave the C2-symmetric 1,3-dicitronellyl-1H- imidazolium bromide (8) (Scheme 3). Differential scanning calorimetry and optical polarizing microscopy revealed smectic mesophases for 1-citronellyl-3-tetradecy-1H-limidazolium bromide (3e) and 1- citronellylpyridinium bromide (6) (Table). In binary mixtures with smectic and nematic liquid crystals 9 and 10, 1-citronellyl-3-methyl-1H-imidazolium bromide (3a) behaved differently. Increasing quantities of 3a cause a decrease of the smectic-phase width for the mixture 3a/9 (Fig. 3), whereas the phase width of the nematic phase for 3a/10 remained nearly constant (Fig. 4).
Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug: Edessa meditabunda
Schulz, Stefan,Szczerbowski, Daiane,Zarbin, Paulo Henrique Gorgatti
, p. 5034 - 5044 (2020)
The male-produced sex pheromone of the stink bug Edessa meditabunda was previously identified as a mixture of the esters methyl 4,8,12-trimethylpentadecanoate (1) and methyl 4,8,12-trimethyltetradecanoate (2), produced in a ratio of 92 : 8, respectively.
New hybrid compounds combining fragments of usnic acid and monoterpenoids for effective tyrosyl-dna phosphodiesterase 1 inhibition
Dyrkheeva, Nadezhda S.,Filimonov, Aleksandr S.,Luzina, Olga A.,Zakharenko, Alexandra L.,Ilina, Ekaterina S.,Malakhova, Anastasia A.,Medvedev, Sergey P.,Reynisson, Jóhannes,Volcho, Konstantin P.,Zakian, Suren M.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
, (2021)
Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabi-lized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3′ end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23–0.40 μM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 μM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan’s cyto-toxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This “protec-tive” effect from topotecan on non-cancerous cells requires further investigation.
Synthesis of the 1,5-dimethylic chiron enantiomers, 3,7,11-trimethyldodec-10-en-1-ol: Application to enantiomeric syntheses of tribolure and a marine fatty acid
Sankaranarayanan,Sharma, Anubha,Chattopadhyay, Subrata
, p. 1373 - 1378 (2002)
A convenient synthesis of the title chiron antipodes has been developed starting from (±)-citronellol via a sequential acetylation protocol using two lipases. The different stereoisomers of the chiron were then functionalized by simple routes to (4R,8R)-dimethyldecanal, an insect pheromone and (5R,9R)-5,9,13-trimethyltetradecanoic acid, a marine phospholipid fatty acid.
Reassignment of the absolute configuration of plakinidone from the sponge consortium Plakortis halichondrioides-Xestospongia deweerdtae using a combination of synthesis and a chiroptical approach
Jiménez-Romero, Carlos,Rode, Joanna E.,Rodríguez, Abimael D.
, p. 410 - 419 (2016)
Recent work by Wu et al. in connection with the first synthesis of the marine natural product plakinidone revealed that the most salient feature of its purported structure, a six-membered perlactone moiety, was in fact a five-membered lactone, i.e. a 3-me
Enantiospecific synthesis of 6-methylheptadec-(9E)-enoic acid enantiomers, the antimicrobial principles of Sporothrix species
Sankaranarayanan, Sivaraman,Chattopadhyay, Subrata
, p. 2627 - 2633 (1998)
An efficient synthesis of the title compound I in both its enantiomeric forms has been developed starting from (R)-citronellol. This involved the introduction of the required alkyl chain and the acidic component at the termini of the starting chiron via judicious derivatization of its bifunctionality to provide the enantiomers of I. The other key features of the synthesis were: (i) use of easily accessible and inexpensive materials/reagents; (ii) operational simplicity; and (iii) brevity.
Photocatalyic Appel reaction enabled by copper-based complexes in continuous flow
Minozzi, Clémentine,Grenier-Petel, Jean-Christophe,Parisien-Collette, Shawn,Collins, Shawn K.
, p. 2730 - 2736 (2018)
A copper-based photocatalyst, Cu(tmp)(BINAP)BF4, was found to be active in a photoredox Appel-type conversion of alcohols to bromides. The catalyst was identified from a screening of 50 complexes and promoted the transformation of primary and secondary alcohols to their corresponding bromides and carboxylic acids to their anhydrides. The protocol was also amendable and optimized under continuous flow conditions.
