- Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage
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An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp3)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.
- Xu, Cheng,Yin, Guodong,Jia, Feng-Cheng,Wu, Yan-Dong,Wu, An-Xin
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supporting information
p. 2559 - 2564
(2021/04/13)
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- 8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity
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A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.
- Dolensky, Johanna,Hochegger, Patrick,Kaiser, Marcel,M?ser, Pascal,Saf, Robert,Seebacher, Werner,Weis, Robert
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- High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates
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Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.
- Gallou, Fabrice,Li, Xiaohan,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.
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supporting information
p. 8114 - 8118
(2021/10/25)
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- Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines
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Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.
- Zhao, Huaibo,Leonori, Daniele
-
supporting information
p. 7669 - 7674
(2021/03/08)
-
- Synthesis and biological evaluation of benzhydryl-based antiplasmodial agents possessing Plasmodium falciparum chloroquine resistance transporter (PfCRT) inhibitory activity
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Due to the surge in resistance to common therapies, malaria remains a significant concern to human health worldwide. In chloroquine (CQ)-resistant (CQ-R) strains of Plasmodium falciparum, CQ and related drugs are effluxed from the parasite's digestive vacuole (DV). This process is mediated by mutant isoforms of a protein called CQ resistance transporter (PfCRT). CQ-R strains can be partially re-sensitized to CQ by verapamil (VP), primaquine (PQ) and other compounds, and this has been shown to be due to the ability of these molecules to inhibit drug transport via PfCRT. We have previously developed a series of clotrimazole (CLT)-based antimalarial agents that possess inhibitory activity against PfCRT (4a,b). In our endeavor to develop novel PfCRT inhibitors, and to perform a structure-activity relationship analysis, we synthesized a new library of analogues. When the benzhydryl system was linked to a 4-aminoquinoline group (5a-f) the resulting compounds exhibited good cytotoxicity against both CQ-R and CQ-S strains of P. falciparum. The most potent inhibitory activity against the PfCRT-mediated transport of CQ was obtained with compound 5k. When compared to the reference compound, benzhydryl analogues of PQ (5i,j) showed a similar activity against blood-stage parasites, and a stronger in vitro potency against liver-stage parasites. Unfortunately, in the in vivo transmission blocking assays, 5i,j were inactive against gametocytes.
- Relitti, Nicola,Federico, Stefano,Pozzetti, Luca,Butini, Stefania,Lamponi, Stefania,Taramelli, Donatella,D'Alessandro, Sarah,Martin, Rowena E.,Shafik, Sarah H.,Summers, Robert L.,Babij, Simone K.,Habluetzel, Annette,Tapanelli, Sofia,Caldelari, Reto,Gemma, Sandra,Campiani, Giuseppe
-
supporting information
(2021/03/08)
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- Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
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A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.
- Todorov, Aleksandar R.,Aikonen, Santeri,Muuronen, Mikko,Helaja, Juho
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supporting information
p. 3764 - 3768
(2019/05/24)
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- Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway
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An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
- Sen, Chiranjit,Sahoo, Tapan,Singh, Harshvardhan,Suresh, Eringathodi,Ghosh, Subhash Chandra
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p. 9869 - 9896
(2019/08/20)
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- Uncatalyzed, on water oxygenative cleavage of inert C-N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives
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Oxygenative cleavage of an inert CAr-NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C-N bond cleavage are incorporated into the target molecule and is effected without the need for N-oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.
- Botla, Vinayak,Pilli, Navyasree,Malapaka, Chandrasekharam
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supporting information
p. 1735 - 1742
(2019/04/08)
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- Systematic ligand variation to modulate the electrochemical properties of iron and manganese complexes
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A series of iron(+iii) and manganese(+ii) complexes based on the dpaqR-ligand system (dpaq = 2-[bis(pyridine-2-ylmethyl)]amino-N-quinolin-8-yl-acetamide) were investigated using cyclic voltammetry (CV) to elucidate how the electronic properties of the ligands influence the overpotential and catalytic current in the context of water oxidation catalysis. For the Fe-complexes an electron withdrawing NO2 or CF3 group attached to the 5-position of the quinoline unit increased the catalytic current, but only with a simultaneous increase of the overpotential. However, when a pyrene moiety was attached to the dipicolylamine unit of the ligand, the overpotential decreased with concomitant increase of the catalytic current. Although the manganese complexes showed no reversible formation of a molecular catalytically active species for water oxidation, the variations of the ligand scaffold affected largely the same trends in their electrochemical behavior.
- Rohner, Stefan S.,Kinzel, Niklas W.,Werlé, Christophe,Leitner, Walter
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supporting information
p. 13205 - 13211
(2019/09/18)
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- Influence of Functionalized Substituents on the Electron-Transfer Abilities of Copper Guanidinoquinoline Complexes
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The influence of functionalized ligands on the electron-transfer abilities of copper guanidinoquinoline complexes as entatic state models has been examined. An electron donating group (OCH3) or electron withdrawing group (Br) was introduced in 6-position of the quinoline unit of the ligands TMGqu and DMEGqu. The electron self-exchange rates k11 of the copper complexes with these ligands were determined using the Marcus cross relation. The k11 values of the functionalized complexes are smaller or equal to the values of their unsubstituted forms. These results were complemented by the examination of the reorganization energies of the electron-transfer via Eyring theory and DFT calculations. The higher reorganization energies of the [Cu(DMEG6Xqu)2]+/2+ (X = H, Br, OCH3) systems correspond with their decelerated electron-transfer velocities. Additionally, the calculated molecular electrostatic potentials show the influence of the functional groups on the electron-transfer. With the addition of the substituent a further charge distribution over the CH3O-/Br-group leads to a larger reorganization required during the oxidation reaction. The impact of the functionalization of the ligand on the electron-transfer of the [Cu(GUA6Xqu)2]+/2+ cations reveals a closer insight in the electronic structure of the complexes and its influence on their electron-transfer abilities.
- Stanek, Julia,Konrad, Marc,Mannsperger, Johannes,Hoffmann, Alexander,Herres-Pawlis, Sonja
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p. 4997 - 5006
(2018/12/11)
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- Synthesis of primaquine glyco-conjugates as potential tissue schizontocidal antimalarial agents
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Primaquine (PQ) is the only drug used to prevent relapse of malaria due to P. vivax and P. ovale, by eradicating the dormant liver form of the parasite (hypnozoites). The side-effects associated with PQ limits is uses in treatment of malaria. To overcome the premature oxidative deamination and to increase the life span of drug in the biological system, the novel glyco-conjugates of PQ were synthesized by coupling of primaquine with hexoses in phosphate buffer. The saccharide part of the hybrid molecules thought to direct the drug to the liver, where hypnozoites resides. All the synthesized compounds were fully characterized and evaluated for their radical curative activities. The three compounds viz glucoside (15a), galactoside (15b) and mannoside (15c) with high activity were tested for their activity in rhesus monkeys where the most active compound 15b showed twofold activity (100% radical curative activity at 1.92?mmol/kg) than the standard drug PQ diphosphate (3.861?mmol/kg). It is proposed that results from these studies may be advantageous to develop a new potent tissue schizonticide antimalarial compound.
- Azad, Chandra S.,Saxena, Mridula,Siddiqui, Arif J.,Bhardwaj, Jyoti,Puri, Sunil K.,Dutta, Guru P.,Anand, Nitya,Saxena, Anil K.
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p. 254 - 261
(2017/07/13)
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- Novel squaramides with in vitro liver stage antiplasmodial activity
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A structure-activity relationship study was performed with ten 8-aminoquinoline-squaramides compounds active against liver stage malaria parasites, using human hepatoma cells (Huh7) infected by Plasmodium berghei parasites. In addition, their blood-schizontocidal activity was assessed against chloroquine-resistant W2 strain Plasmodium falciparum. Compound 3 was 7.3-fold more potent than the positive control primaquine against liver-stage parasites, illustrating the importance of the squarate moiety to activity.
- Ribeiro, Carlos J.A.,Espadinha, Margarida,Machado, Marta,Gut, Jiri,Gon?alves, Lídia M.,Rosenthal, Philip J.,Prudêncio, Miguel,Moreira, Rui,Santos, Maria M.M.
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p. 1786 - 1792
(2016/04/05)
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- 5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives
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We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.
- Kuninobu, Yoichiro,Nishi, Mitsumi,Kanai, Motomu
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supporting information
p. 8092 - 8100
(2016/09/09)
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- COMPOSITIONS AND METHODS FOR TREATING AND PREVENTING CANCER
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This invention is in the field of medicinal chemistry. In particular, the invention relates to novel small molecule compounds having a quinolin-8-yl-nicotinamide structure which are useful in treating, ameliorating, or preventing various forms of cancer (e.g., pancreatic cancer).
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Page/Page column 78
(2016/12/12)
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- VEGFR TYROSINE KINASE INHIBITORS
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Novel compounds, their prodrugs, and the pharmaceutically acceptable salts as pharmaceutical compositions containing such compounds useful in treating certain diseases modulated by the inhibition of vascular endothelial growth factors (VEGFs) receptor tyrosine kinases are provided. In particular, compounds and compositions and the methods for the prophylaxis, management and treatment of cancers through the inhibition of VEGF receptor tyrosine kinases are provided.
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Page/Page column 30
(2014/12/12)
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- Novel potent metallocenes against liver stage malaria
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Novel conjugates of the antimalarial drug primaquine (compound 1) with ferrocene, named primacenes, have been synthesized and screened for their activities against blood stage and liver stage malaria in vitro and host-vector transmission in vivo. Both transmission-blocking and blood-schizontocidal activities of the parent drug were conserved only in primacenes bearing a basic aliphatic amine group. Liver stage activity did not require this structural feature, and all metallocenes tested were comparable to or better than primaquine in this regard. Remarkably, the replacement of primaquine's aliphatic chain by hexylferrocene, as in compound 7, led to a ～45-fold-higher level activity against liver stage parasitemia than that of primaquine. Copyright
- Matos, Joana,Da Cruz, Filipa P.,Cabrita, Elia,Gut, Jiri,Nogueira, Fatima,Do Rosario, Virgilio E.,Moreira, Rui,Rosenthal, Philip J.,Prudencio, Miguel,Gomes, Paula
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scheme or table
p. 1564 - 1570
(2012/06/01)
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- Novel Sulfonaminoquinoline Hepcidin Antagonists
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The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.
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Page/Page column 126
(2012/09/05)
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- TRIPLE SUBSTITUTED PHENANTHROLINE DERIVATIVES FOR THE TREATMENT OF NEURODEGENERATIVE OR HAEMATOLOGICAL DISEASES OR CONDITIONS, OR CANCER
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The present invention relates to a new family of triple substituted phenantroline derivatives of formula (I), which are useful for the treatment or profilaxis of a neurodegenerative or haematological disease or condition or cancer, their use as a medicament, especially for treating a neurodegenerative or haematological disease or condition or cancer, and a pharmaceutical composition comprising the compounds.
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Page/Page column 43-44
(2010/06/22)
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- ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
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Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise (I) wherein: Ra, R1, R2 and R3 are each, independently, hydrogen, or a substituent selected from halogen, CF3, alkyl, alkoxy, MeSO2, amino or aminocarbonyl (each optionally substituted by one or two groups selected from alkyl and benzyl) carboxy, or alkoxycarbonyl; or two adjacent of Ra and R1-4 together can form a 5-7 membered carbocyclic or heterocyclic ring which is optionally substituted by a substituent defined above; R4 is hydrogen, halogen, or alkyl; R5 is hydrogen, alkyl, arylalkyl, or aryl; R6 is hydrogen, halogen, CF3, CN, carbamide, alkoxy or benzyloxy; X1, X2 and X3 are each carbon or one of X1, X2 or X3 may be nitrogen; Y is CH or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof.
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-
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- Aryl-8-azabicyclo [3.2.1] octanes for the treatment of depression
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The present invention includes compounds of formula I wherein A, X, n, Ar1, and Ar2 are defined as set forth herein. These compounds may be used to treat depression. The invention also includes formulations containing these compounds, and methods for making and using compounds of this invention.
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- Primaquine-induced hemolytic anemia: Formation and hemotoxicity of the arylhydroxylamine metabolite 6-methoxy-8-hydroxylaminoquinoline
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Primaquine is an important antimalarial agent because of its activity against exoerythrocytic forms of Plasmodium spp. However, methemoglobinemia and hemolytic anemia are dose-limiting side effects of primaquine therapy that limit its efficacy. These hemotoxicities are thought to be mediated by metabolites; however, the identity of the toxic species has remained unclear. Since N-hydroxy metabolites are known to mediate the hemotoxicity of several arylamines, the present studies were undertaken to determine whether 6-methoxy-8-aminoquinoline (6-MAQ), a known human metabolite of primaquine, could undergo N-hydroxylation to form a hemotoxic metabolite. When 6-MAQ was incubated with rat and human liver microsomes, a single metabolite was detected by high performance liquid chromatography (HPLC) with electrochemical detection. This metabolite was identified as 6-methoxy-8-hydroxylaminoquinoline (MAQ-NOH) by HPLC and mass spectral analyses. As measured by decreased survival of 51Cr-labeled erythrocytes in rats, MAQ-NOH was hemolytic in vivo. Furthermore, in vitro exposure of 51Cr-labeled erythrocytes to MAQ-NOH caused a concentration-dependent decrease in erythrocyte survival (EC50 of 350 μM) when the exposed cells were returned to the circulation of isologous rats. MAQ-NOH also induced the formation of methemoglobin when incubated with suspensions of rat erythrocytes. These data indicate that 6-MAQ can be metabolized to MAQ-NOH by both rat and human liver microsomes and that MAQ-NOH has the requisite properties to be a hemotoxic metabolite of primaquine. The contribution of MAQ-NOH to the hemotoxicity of primaquine in vivo remains to be assessed.
- Bolchoz, Laura J. C.,Budinsky, Robert A.,Mcmillan, David C.,Jollow, David J.
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p. 509 - 515
(2007/10/03)
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- 8-Aminoquinolines as anticoccidials - Part III
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Analogues of the antimalarial pentaquine, 1, in which the nature of the side-chain on the 8-amino position was varied, were prepared and evaluated for anticoccidial activity both in vitro and in vivo. Specifically, both the inter-nitrogen distance and the nature of the terminal amino group were investigated. Novel analogues of equal or improved efficacy in vitro and in vivo to pentaquine were discovered.
- Armer, Richard E.,Barlow, Jacqueline S.,Chopra, Narinder,Dutton, Christopher J.,Greenway, David H.J.,Greenwood, Sean D.W.,Lad, Nita,Shaw, Jonothan,Thompson, Adrian P.,Thong, Kam-Wah,Tommasini, Ivan
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p. 2425 - 2430
(2007/10/03)
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- REDUCTION OF HETERO-AROMATIC NITRO COMPOUNDS WITH BAKER'S YEAST
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Reduction of nitro group on hetero-aromatics with baker's yeast has been examined.
- Takeshita, Mitsuhiro,Yoshida, Sachiko
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p. 2201 - 2204
(2007/10/02)
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- Formation, Dealkylation, and Nucleophilic Substitution of Some Mono- and Di-alkoxypyridoazepines
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The photo-induced ring-expansions of 5-azido-, 8-azido-, 6-azido-8-metoxy, and 8-azido-6-metoxy-quinolines to alkoxypyridoazepines in alcohol-alkoxide-dioxane solution containing 18-crown-6 are reported, although in some instances azepinone and/or azepine ring contraction products are noted.In addition, ring-expansions in the presence of phenoxide ion have been achieved for the first time. 1H N.m.r. spectra indicate that some of the pyrido-azepines and -azepinones are formed as mixtures of the 5H- and 7H-isomers.Dealkylations and nucleophilic substitution of the alkoxypyridoazepines are discussed,the latter in some instances being accompanied by ring-contraction to diaminoquinolines.
- Patel, Dalpat I.,Scriven, Eric F. V.,Smalley, Robert K.,Suschitzky, Hans
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p. 1911 - 1916
(2007/10/02)
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- Unusual Ring Opening Through C-C Bond Cleavage in 4-Methoxy-2-methyl-3-oxo(1H)-2,3-dihydropyrroloquinoline
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Unusual ring opening and C-C cleavage in 4-methoxy-2-methyl-3-oxo(1H)-2,3-dihydropyrroloquinoline (1) during alkylation with alkyl halides in the presence of sodium hydroxide in methanol yield 8-(2-alkoxycarbonylethyl)amino-6-methoxyquinolines (2 and 3) and 8-amino-6-methoxyquinoline (4).A plausible mechanism of the formation of these compounds has been discussed.
- Bhat, Balkrishen,Bhaduri, A. P.
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- Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes
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A number of hydroxy analogues of the antimalarial drug primaquine [8-[(4-amino-1-methylbutyl)amino]-6-methoxyquinoline] were synthesized and characterized by 1H NMR and mass spectra. Several of the compounds were found to be active in forming methemoglobin in human erythrocytes, particularly in those from glucose-6-phosphate dehydrogenase (G6PD) deficient subjects. Decreased levels of glutathione (GSH) in G6PD-deficient erythrocytes were also found with compounds that were active methemoglobin formers.
- Allahyari,Strother,Fraser,Verbiscar
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p. 407 - 410
(2007/10/02)
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- Bromo-6-methoxy-8-aminoquinolines: Preparation and 13C-NMR assignments
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Preparation of all possible monobromo-6-methoxy-8-aminoquinolines is reported. These materials provided an opportunity to assess the effect of bromine substitution on 13C-NMR chemical shift patterns. An explanation of the isomerization of 5-bromo-6-methoxy-8-acetamidoquinoline to 7-bromo-6-methoxy-8-aminoquinoline during hydrolysis is presented.
- McChesney,Sarangan,Hufford
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p. 1854 - 1856
(2007/10/02)
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- The Photo-induced Ring Expansion of Azido(methoxy)quinolines to Methoxypyridoazepines
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The yield of 9-alkylamino-5H-pyridoazepines from the photo-induced ring-expansion of 8-azidoquinoline in primary amines are increased significantly by the presence of a 6-methoxy group, which also for the first time induces ring-expansion of the azide in secondary amines.Optimum conditions have been found for the ring-expansion of 8-azidoquinoline in methanol-potassium methoxide to give 9-methoxy-5H-pyridoazepine, and under the same conditions 8-azido-6-methoxy- and 6-azido-8-methoxy-quinoline ring-expand in excellent yield to the corresponding dimethoxypyridoazepines.
- Khan, Zafar U.,Patel, Dalpat I.,Smalley, Robert K.,Scriven, Eric F.V.,Suschitzky, Hans
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p. 2495 - 2500
(2007/10/02)
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- Photolysis of Quinolyl Azides in Aliphatic Thiols. Synthesis of o-Alkylthioquinolylamine
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Photolysis of 5- or 8-quinolyl azide in various thiols gives o-alkylthioquinolylamines.The beneficial effect of a 6-methoxy-group in 8-quinolyl azide on the yields is noted.
- Khan, Zafar U.,Nay, Barry,Scriven, Eric F.V.,Suschitsky, Hans
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p. 671 - 672
(2007/10/02)
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