35278-77-4Relevant academic research and scientific papers
First total synthesis of a guanidine alkaloid Nitensidine D using immobilized ionic liquid, microwaves and formamidinesulfinic acid
Shallu,Sharma,Singh, Jasvinder
, p. 1869 - 1874 (2014)
An efficient first total synthesis of a naturally occurring guanidine alkaloid, Nitensidine D isolated from ethanol extract of Pterogyne nitens has been described. Geraniol has been used as the starting material. N-alkylation of phthalimide has been achieved using immobilized ionic liquid and formamidinesulfinic acid acts as the guanylating reagent. [Figure not available: see fulltext.]
ETHYLENEDIAMINE COMPOUND AND USE THEREOF
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Paragraph 0220-0222, (2021/11/04)
The present invention relates to the field of medicinal chemistry, and relates to an ethylenediamine compound represented by Formula A, pharmaceutically acceptable salts, stereoisomers, tautomers or isomer mixtures, hydrates thereof, solvates thereof, or prodrugs thereof, and use thereof in the treatment of tuberculosis.
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.
, (2021/07/02)
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.
ANTIBIOTIC COMPOUNDS
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Paragraph 00118, (2021/04/02)
Provided herein are lipidated glycopeptide compounds of formula (I); or a pharmaceutically acceptable salt, stereoisomer, solvate, or prodrug thereof. R1 is a lipid, R2 is -H or a lipid, and R3 and R4 are as defined herein. These compounds have antibiotic activity. Also provided are formulations comprising such compounds; as well as such compounds or formulations for use as a medicament. The compounds and formulations may also be used in the treatment of bacterial infection.
New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections
Agafonov, Alexander P.,Bormotov, Nikolay I.,Korchagina, Dina V.,Maksyutov, Rinat A.,Mozhaytsev, Evgenii S.,Salakhutdinov, Nariman F.,Serova, Olga A.,Shishkina, Larisa N.,Suslov, Evgenii V.,Volcho, Konstantin P.,Yarovaya, Olga I.
, p. 1185 - 1195 (2020/11/03)
Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components. The produced compounds exhibited high activity against the vaccinia virus (an enveloped virus belonging to the poxvirus family), which was combined with low cytotoxicity. Some compounds had a selectivity index higher than that of the reference drug cidofovir; the highest SI = 1123 was exhibited by 1-adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene moiety. The produced compounds demonstrated inhibitory activity against other orthopoxviruses: cowpox virus (SI = 30-406) and ectromelia virus (mousepox virus, SI = 39-707). This journal is
Platinum-(phosphinito-phosphinous acid) complexes as bi-talented catalysts for oxidative fragmentation of piperidinols: An entry to primary amines
Membrat, Romain,Vasseur, Alexandre,Moraleda, Delphine,Michaud-Chevallier, Sabine,Martinez, Alexandre,Giordano, Laurent,Nuel, Didier
, p. 37825 - 37829 (2019/12/03)
Platinum-(phosphinito-phosphinous acid) complex catalyzes the oxidative fragmentation of hindered piperidinols according to a hydrogen transfer induced methodology. This catalyst acts successively as both a hydrogen carrier and soft Lewis acid in a one pot-two steps process. This method can be applied to the synthesis of a wide variety of primary amines in a pure form by a simple acid-base extraction without further purification.
Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids
Oberhauser, Clara,Harms, Vanessa,Seidel, Katja,Schr?der, Benjamin,Ekramzadeh, Kimia,Beutel, Sascha,Winkler, Sven,Lauterbach, Lukas,Dickschat, Jeroen S.,Kirschning, Andreas
supporting information, p. 11802 - 11806 (2018/09/10)
The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.
Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts
Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Alshammari, Ahmad S.,Pohl, Marga-Martina,Beller, Matthias,Jagadeesh, Rajenahally V.
, p. 8553 - 8560 (2018/11/30)
The development of efficient and selective nanostructured catalysts for industrially relevant hydrogenation reactions continues to be an actual goal of chemical research. In particular, the hydrogenation of nitriles and nitroarenes is of importance for the production of primary amines, which constitute essential feedstocks and key intermediates for advanced chemicals, life science molecules and materials. Herein, we report the preparation of graphene shell encapsulated Co3O4- and Co-nanoparticles supported on carbon by the template synthesis of cobalt-terephthalic acid MOF on carbon and subsequent pyrolysis. The resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale and recycling of the catalyst.
3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis
Sakamoto, Izumi,Iwaoka, Kazuya,Kawada, Yuta,Naito, Takanori,Makida, Kazuyoshi,Takeuchi, Yuki,Nishii, Takeshi,Horikawa, Mitsuyo,Kaku, Hiroto,Tsunoda, Tetsuto
, p. 3052 - 3060 (2018/05/23)
3,3-Dimethoxypropylsulfonyl (Dimps) chloride was prepared and used as a new versatile sulfonating agent for ammonia, primary and secondary amines to afford corresponding Dimps-amides in excellent yields. The resulting N-nonsubstituted and N-monosubstituted Dimps-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions. The Dimps group was removed by treatment in aqueous solution under acidic followed by basic conditions. Furthermore, epilachnene, the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized utilizing this Dimps methodology in short steps.
Antiparasitic activity of sulfur- and fluorine-containing bisphosphonates against trypanosomatids and apicomplexan parasites
Galaka, Tamila,Casal, Mariana Ferrer,Storey, Melissa,Li, Catherine,Chao, María N.,Szajnman, Sergio H.,Docampo, Roberto,Moreno, Silvia N.J.,Rodriguez, Juan B.
, (2017/01/24)
Based on crystallographic data of the complexes 2-alkyl(amino)ethyl-1,1-bisphosphonates-Trypanosoma cruzi farnesyl diphosphate synthase, some linear 1,1-bisphosphonic acids and other closely related derivatives were designed, synthesized and biologically evaluated against T. cruzi, the responsible agent of Chagas disease and against Toxoplasma gondii, the etiologic agent of toxoplasmosis and also towards the target enzymes farnesyl pyrophosphate synthase of T. cruzi (TcFPPS) and T gondii (TgFPPS), respectively. The isoprenoid-containing 1,1-bisphosphonates exhibited modest antiparasitic activity, whereas the linear α-fluoro-2-alkyl(amino)ethyl-1,1-bisphosphonates were unexpectedly devoid of antiparasitic activity. In spite of not presenting efficient antiparasitic activity, these data turned out to be very important to establish a structural activity relationship.
