cas 20511-12-0, 2-Amino-5-iodopyridine | Articles data

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Synthesis of 2,3-Disubstituted 5-Iodo-1H-Pyrrolo[2,3-b]pyridines via Fischer Cyclization
A simple and convenient procedure for the preparation of some unknown 2,3-disubstituted 5-iodo-1H-pyrrolo[2,3-b]pyridines from readily available starting materials by Fischer indole cyclization in polyphosphoric acid is described. The present methodology provides an alternative synthetic approach to the synthesis of 5-iodo-7-azaindole scaffold. All synthesized compounds were characterized by IR, MS, 1H and 13C NMR, and elemental analysis.
Alekseyev, Roman S.,Amirova, Sabina S.,Terenin, Vladimir I.
p. 2656 - 2663
(2017)
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NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl
In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.
Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh
p. 12467 - 12474
(2021/08/24)

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes
Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information

(2021/05/26)

Method for preparing 4 - (6 -aminopyridine -3 -yl) piperazine -1 - carboxylic acid tert-butyl ester
The invention discloses a method for preparing 4 - (6 - aminopyrid -3 -yl) piperazine -1 - carboxylic acid tert-butyl ester, which comprises the following steps of: reacting 2 - aminopyridine with iodine to generate 2 - amino -5 -iodopyridine. Step II: 2 - amino -5 -iodopyridine was subjected to a coupling reaction to obtain 4 - (6 - aminopyrid -3 -yl) piperazine -1 -carboxylic acid tert-butyl ester. The method has the advantages of short synthetic route, high target product yield and low cost.
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Paragraph 0042-0049; 0054-0061; 0066-0072

(2021/09/26)

BICYCLIC KINASE INHIBITORS AND USES THEREOF
The invention relates to kinase inhibitors, in particular inhibitors of protein kinases including the SIK-family, CSF1R, HCK, TEK-family, BRK, ABL, KIT and/or their mutants. Although structurally similar to other bicyclic kinase inhibitors, the kinase inhibitors of the invention are distinctive; possessing a particular class of heterocyclic moiety. Such kinase inhibitors can display one or more certain properties distinct to their structurally similar kinase inhibitors. The kinase inhibitors of the invention or pharmaceutical compositions comprising them may be used in the treatment of a disorder or condition, such as a proliferative disorder, for example, a leukaemia or solid tumour. In particular, these and other structurally related kinase inhibitors may be used in the treatment of a proliferative disorder - such as a mixed phenotype acute leukaemia (MPAL) - characterised by (inter-alia) the presence of MEF2C protein, a human chromosomal translocation at 11q23, and/or a KMT2A fusion oncoprotein. The kinase inhibitors or pharmaceutical compositions of the invention may be used topically to modulate skin pigmentation in a subject, for example to impart UV protection and reduce skin cancer risk.
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Paragraph 613; 625

(2021/11/06)

CN-Modified Imidazopyridine as a New Electron Accepting Unit of Thermally Activated Delayed Fluorescent Emitters
Two efficient thermally activated delayed fluorescent (TADF) emitters were developed by utilizing CN-modified imidazopyridine as an acceptor unit. The CN-modified imidazopyridine acceptor was combined with either an acridine donor or a phenoxazine donor through a phenyl linker to produce two TADF emitters, Ac-CNImPy and PXZ-CNImPy. The acridine-based Ac-CNImPy emitter exhibited sky-blue emission with a CIE coordinate of (0.18, 0.38), whereas the phenoxazine-donor-based PXZ-CNImPy showed greenish-yellow emission with a CIE coordinate of (0.32, 0.58). A high photoluminescence quantum yield of 80 % was observed for the PXZ-CNImPy emitter compared with 40 % for the Ac-CNImPy emitter. Organic light-emitting diodes based on the PXZ-CNImPy emitter demonstrated high external quantum efficiency of 17.0 %. Hence, the CN-modified imidazopyridine unit can be considered as a useful electron acceptor for the future design of highly efficient TADF emitters.
Kothavale, Shantaram,Lee, Jun Yeob,Lee, Kyung Hyung
(2020/01/21)

2-amino-5-iodopyridine synthesis method
The invention discloses a 2-amino-5-iodopyridine synthesis method, which comprises: (1) dissolving 2-aminopyridine in water; (2) adding iodine in 3-5 batches while stirring, and keeping the temperature for 2 h after the iodine is added; (3) after thermal insulation is finished, adding hydrogen peroxide in a dropwise manner, and continuously carrying out thermal insulation for 2-3 h after the adding; and (4) after the reaction is finished, carrying out heating reflux for 20-30 min, cooling and filtering, rinsing a filter cake with ice water, and drying to obtain the 2-amino-5-iodopyridine. According to the present invention, water is used as the solvent for synthesis, and no organic solvent is used, such that the reaction process is safe and free of pollution.
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Paragraph 0013-0024

(2020/01/08)

BICYCLIC COMPOUND AND USE THEREOF FOR INHIBITING SUV39H2
The present invention directs to a compound represented by formula (I).
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Page/Page column 233; 234

(2017/08/01)

Self-assembly of heteroleptic dinuclear metallosupramolecular kites from multivalent ligands via social self-sorting
A Tr?ger's base-derived racemic bis(1,10-phenanthroline) ligand (rac)-1 and a bis(2,2′-bipyridine) ligand with a central 1,3-diethynylbenzene unit 2 were synthesized. Each of these ligands acts as a multivalent entity for the binding of two copper(I) ions. Upon coordination to the metal ions these two ligands undergo selective self-assembly into heteroleptic dinuclear metallosupramolecular kites in a high-fidelity social self-sorting manner as evidenced by NMR spectroscopy and mass spectrometry.
Benkh?user, Christian,Lützen, Arne
p. 693 - 700
(2015/06/08)

Ionic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes
Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.
Nouzarian, Mahboobe,Hosseinzadeh, Rahman,Golchoubian, Hamid
supporting information
p. 2913 - 2925
(2013/09/02)

NICOTINIC RECEPTOR COMPOUNDS
Provided herein are compounds and methods of preparation of compounds that are capable of functioning as agonists or antagonists of a nicotinic receptor. Also provided are pharmaceutical compositions comprising one or more of these compounds, which may further comprise one or more additional therapeutic agents. Further provided are methods of treatment of various conditions that may be responsive to such activity at the nicotinic receptors, such as nicotine dependence.
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Page/Page column 42

(2012/03/11)

Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene
Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.
Shen, Hao,Vollhardt, K. Peter C.
supporting information; experimental part
p. 208 - 214
(2012/03/11)

Hydrodehalogenation of aryl chlorides and aryl bromides using a microwave-assisted, copper-catalyzed concurrent tandem catalysis methodology
A concurrent tandem catalytic methodology has been developed for the hydrodehalogenation of aryl bromides and aryl chlorides. The first step of the tandem catalytic cycle, halogen exchange, produced yields of 84-97% from aryl bromides using 5 mol % CuI catalyst, 10 mol % N,N′-dimethylcyclohexane-1, 2-diamine (1), and 2 equiv of NaI in acetonitrile under microwave radiation at 100 C in 0.5-1.5 h. The same reaction for aryl chlorides appeared to be equilibrium-limited after 1 hour at 200 C (yields of 5-44%). Both aryl bromides and aryl chlorides were hydrodehalogenated in 12-87% yield using 20 mol % CuI, 1.5 equiv of diamine 1, and 2 equiv of NaI in acetonitrile at 200 C after 1-2 h. Substrates with oxygen- or nitrogen-containing functional groups had substantially lower yields than hydrocarbon substrates. Deuterium labeling studies suggest that diamine 1 supplies the majority of the hydrogen for the hydrodehalogenation reaction, but solvent can also serve as a source. This article not subject to U.S. Copyright. Published 2011 by the American Chemical Society.
Cannon, Kathleen A.,Geuther, Meagan E.,Kelly, Colin K.,Lin, Shirley,MacArthur, Amy H. Roy
experimental part
p. 4067 - 4073
(2011/10/03)

6-Substituted 2-(N-trifluoroacetylamino)imidazopyridines induce cell cycle arrest and apoptosis in SK-LU-1 human cancer cell line
A series of 6-substituted 2-(N-trifluoroacetylamino)imidazopyridines have been synthesized and their bioactivities were evaluated. Compounds 6a, 6c, and 11a were the most active compounds with modest cytotoxic activity against six human cancer cell lines U251 (glioma), PC-3 (prostate), K-562 (leukemia), HCT-15 (colon), MCF7 (breast) and SK-LU-1 (lung). The cell cycle analysis showed that compounds 6a, 6c, and 11a induce a G2/M phase cell cycle arrest on SK-LU-1 cell line where inhibition of CDK-1 and CDK-2 may be implicated.
Martínez-Urbina, Miguel Angel,Zentella, Alejandro,Vilchis-Reyes, Miguel Angel,Guzmán, ángel,Vargas, Omar,Ramírez Apan, María Teresa,Ventura Gallegos, José Luis,Díaz, Eduardo
experimental part
p. 1211 - 1219
(2010/05/02)

A practical iodination of aromatic compounds by using iodine and iodic acid
This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product. Copyright Taylor & Francis Group, LLC.
Shinde, Avinash T.,Zangade, Sainath B.,Chavan, Shivaji B.,Vibhute, Archana Y.,Nalwar, Yogesh S.,Vibhute, Yeshwant B.
experimental part
p. 3506 - 3513
(2011/02/22)

Synthesis and helicate formation of a new family of binol-based bis(bipyridine) ligands
A new family of BINOL-based bis(bipyridine) ligands 1-3 (BINOL = 2,2 -dihydroxy-1,1 -binaphthyl) was prepared in enantiomerically pure form. Whereas the coordination of zinc(ll) ions to these ligands did not result in the selective formation of a specific metallosupramolecular aggregate,1 -3 were found to undergo highly diastereoselective self-assembly to D 2-symmetric dinuclear double-stranded helicates upon coordin ation to silver(l) and copper(l) ions and to D3-symmetric dinuclear triple-stranded helicates upon coordination to iron(ll) as demonstrated by mass spectrometry and by NMR and CD spectroscopy in combination with quantum chemical calculations.
Bunzen, Jens,Bruhn, Torsten,Bringmann, Gerhard,Luetzen, Arne
scheme or table
p. 3621 - 3630
(2009/08/14)

Surprising substituent effects on the self-assembly of helicates from bis(bipyridyl) BINOL ligands
(Figure Presented) A number of different bis(bipyridyl) BINOL ligands were prepared using a convergent building block approach. These were studied with regard to their ability to undergo self-assembly to dinuclear helicates upon coordination to suitable late-transition-metal ions. Surprisingly, the substituents at the periphery of the ligand structure were found to have a marked influence on the outcome of the self-assembly processes with regard to the helicates composition, the stereoselectivity of the helicate formation, their redox reactivity, and their electronical properties as scrutinized by NMR- and CD-spectroscopic methods as well as ESI-mass spectrometric methods.
Bunzen, Jens,Hovorka, Rainer,Luetzen, Arne
supporting information; scheme or table
p. 5228 - 5236
(2009/12/04)

Immobilization of bis(bipyridine) BINOL ligands and their use in chiral resolution
An enantlomerlcally pure bls(blpyrldlne) BINOL ligand was synthesized which was functionalized with an Iodine substituent In Its periphery. Using this halogen function, the ligand was Immobilized on a commercially available polystyrene gel via Suzuki cross-coupling. The functlonallzed gel was found to be effective In the chiral resolution of similar bis(blpyrldlne) ligands based on a Troeger's base core.
Bunzen, Jens,Kiehne, Ulf,Benkhaeuser-Schunk, Christian,Luetzen, Arne
supporting information; scheme or table
p. 4786 - 4789
(2009/12/29)

The influence of different spacer lengths on the selectivity of self-assembly processes of bis(bipyridine)-BINOL helicates
The synthesis and self-assembly behaviour of a series of en-antiomerically pure bis(chelating) ligands is reported. The li-gands differ in the spacer unit between a BINOL core and. two bipyridyl groups as the chelating entities and were found to undergo completely diastereoselective self-assembly to di-nuclear double-stranded helicates with silver(I) salts, as dem-onstrated by NMR and CD spectroscopy and ESI mass spec-trometry. Upon coordination to iron(II) or zinc(II) ions, however, a dramatic loss in the diastereoselectivity of the self-assembly of dinuclear triple-stranded helicates was observed, as a result: of increasing spacer length. In the case of zinc(II), the self-assembly processes were even found, to be nonselec-tive with regard to the composition of the helicates.
Bunzen, Jens,Hapke, Marko,Luetzen, Arne
scheme or table
p. 3885 - 3894
(2010/01/18)

Novel saccharide-pyridine based gelators: Selective gelation and diversity in superstructures
A series of N-glycosylamine based organogelators were synthesized from 4,6-O-protected saccharides introducing pyridylamines. The gelation properties of these compounds were studied in regard to their molecular structure by scanning electron microscopy, differential scanning calorimetry, FT-IR spectroscopy and quantum chemical calculations. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.
Kumar, K. Karthik,Elango,Subramanian,Das, T. Mohan
experimental part
p. 1570 - 1577
(2009/10/30)

A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants
(Chemical Equation Presented) A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.
Nara, Susheel J.,Jha, Mukund,Brinkhorst, Johan,Zemanek, Tony J.,Pratt, Derek A.
supporting information; experimental part
p. 9326 - 9333
(2009/04/06)

HIV INHIBITING 3,4-DIHYDRO-IMIDAZO[4,5-B]PYRIDIN-5-ONES
HIV inhibitory compounds of formula (I) salts, hydrates, solvates, N-oxides, or stereoisomers thereof, wherein A forms pyridine, pyrimidine, pyrazine, pyridazine, triazine, imidazole, pyrazole, triazole, tetrazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, and thiadiazole; R1 is halo, cyano, nitro, C1-6alkyl, polyhaloC1-6alkyl, -C1-6alkyl-OR4, -C(=O)-R5, -C(=O)-OR4, -C(=O)-NR6R7, -OR4, -O-C(=O)-C1-6alkyl, -O-C1-6alkyl-OR4, -O-C1-6alkyl-NR6R7, -O-C1-6alkyl-O-C(=O)-C1-6Alkyl, -O-C1-6alkyl-C(=O)-OR4, -O-C1-6alkyl-C(=O)-NR6R7, -NR6R7, -NR8-C(=O)-R5, -NR8-C(=O)-OR4, -NR8-C(=O)-NR6R7, -NR8-C(=O)-C1-6lkyl-C(=O)-OR4, -NR8-C1-6alkyl-OR4, -NR8-C1-6alkyl-NR6R7, -NR8-C1-6alkyl-imidazo lyl, -NR8-SO2R9, -N=CH-NR6R7, -NH-C(=NH)-NH2, -SO2NR6R7, and -O-PO(OR8)2; D forms pyridine, pyrimidine, pyrazine, pyridazine, pyrrole, imidazole, pyrazole, furane, oxazole, isoxazole, thiophene, thiazole, and isothiazole; R2 is C1-6alkyl, polyhaloC1-6alkyl, halo, cyano, -COOR4, -OR4, and -NR6R7; R3 is phenyl, pyridyl, pyrimidinyl, imidazopyridyl, pyrazolopyridyl, triazolopyridyl, quinoline, imidazopyrimidinyl, pyrazolopyrimidinyl, triazolopyrimidinyl, pyridopyrimidinyl; which may optionally be substituted; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; 25 pharmaceutical compositions containing these compounds, methods for preparing these compounds and compositions.
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Page/Page column 40-41

(2008/06/13)

POLYCYCLIC PYRIMIDINES AS POTASSIUM ION CHANNEL MODULATORS
The present invention provides a genus of polycyclic pyrimidines that are useful as modulators of potassium ion channels. The modulators of the invention are of use in both therapeutic and diagnostic methods.
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Page/Page column 35

(2008/06/13)

POLYCYCLIC PYRIDINES AS POTASSIUM ION CHANNEL MODULATORS
The present invention provides a genus of polycyclic pyridines that are useful as modulators of potassium ion channels. The modulators of the invention are of use in both therapeutic and diagnostic methods.
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Page/Page column 43

(2010/02/14)

Polycyclic pyrazines as potassium ion channel modulators
The present invention provides a genus of polycyclic pyrazines that are useful as modulators of potassium ion channels. The modulators of the invention are of use in both therapeutic and diagnostic methods.
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Page/Page column 10; 16

(2010/02/14)

PHENYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
The present invention is directed to phenylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.
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Page 76

(2010/02/07)

COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS
One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.
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Page 42-43; 83

(2010/02/06)

An HIV reverse transcriptase-selective nucleoside chain terminator
The synthesis of a 2-,3-dideoxynucleoside cytidine analogue, but one that lacks the O2-carbonyl, is described from 2-aminopyridine in an overall yield of 60%. The synthesis of the 2-pyridone C-nucleoside relies upon the use of a Heck-type coupling between an appropriately protected sugar glycal and the 5-iodo derivative of 2-aminopyridone. Upon conversion of the dideoxynucleoside to the corresponding 5-triphosphate, the analogue ddNTP is observed to be a reasonable substrate with HIV reverse transcriptase (for a template dG residue), but is not a substrate for calf thymus DNA polymerase α or for human DNA polymerase β. With the human mitochondrial DNA polymerase the analogue functions as a poor substrate. The observed polymerase selectivities appear to arise from the absence of the O2-carbonyl, which either results in a destabilized Watson-Crick base pair or represents a critical contact for some polymerases. Copyright
Fraley, Andrew W.,Chen, Dongli,Johnson, Kenneth,McLaughlin, Larry W.
p. 616 - 617
(2007/10/03)

Synthesis of Differently Disubstituted 2,2′-Bipyridines by a Modified Negishi Cross-Coupling Reaction
A general practical approach to a number of differently disubstituted 2,2′-bipyridines from substituted 2-bromo- and 2-chloropyridines by application of modified Negishi cross-coupling conditions has been developed. These 2,2′-bipyridines carry versatile functional groups that can be elaborated further, as demonstrated for some examples. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Luetzen, Arne,Hapke, Marko,Staats, Holger,Bunzen, Jens
p. 3948 - 3957
(2007/10/03)

Compounds and methods for promoting smoking cessation
Compounds and methods for promoting smoking cessation. The compounds may be used to treat a variety of other conditions and disease states.
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(2008/06/13)

Selective anti-viral nucleoside chain terminators
The present invention relates to dideoxynucleoside analog compounds containing a dideoxy ribofuranosyl moiety that exhibit selective anti-viral activity coupled with substantially low toxicity toward the host cells. In particular, the compounds according to the present invention show potent inhibition of the replication of the human immunodeficiency virus (HIV), while remaining substantially inert toward host cell DNA. Compounds according to the present invention exhibit primary utility as agents for inhibiting the growth or replication of retroviruses, particularly HIV. The compounds of the invention comprise a (2,3 ′-dideoxy-β-ribofuranosyl) ring coupled to a heterocyclic nucleobase that lacks an “O2 carbonyl”, that enables them to selectively react with and inhibit viral reverse transcriptase, while remaining substantially unreactive toward human DNA polymerases.
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(2008/06/13)

Copper-catalyzed halogen exchange in aryl halides: An aromatic finkelstein reaction
A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of Cul and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using Nal as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents. Copyright
Klapars, Artis,Buchwald, Stephen L.
p. 14844 - 14845
(2007/10/03)

Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters
This paper describes a general method for the synthesis and isolation of novel 6-halo-pyridin-3-yl-boronic acids and esters 2-5. These compounds are prepared taking in account a regioselective halogen-metal exchange with a trialkylborate starting from 2,5-dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with a range of arylhalides and authorise a strategy to produce new pyridines libraries.
Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valérie,Bovy, Philippe R,Rault, Sylvain
p. 2885 - 2890
(2007/10/03)

Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2′-substituted 5′-pyridinyl)-7-azabicyclo[2.2.1]heptanes. Epibatidine analogues
A convenient, high-yield synthesis of 7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2-ene (5), which involved the addition of tributyltin hydride to 7-tert-butoxycarbonyl-2-p-toluenesulfonyl-7-azabicyclo[2.2.1]hept-2-ene (4) followed by elimination of the tributyltin and p-tolylsulfonyl groups using tetrabutylammonium fluoride was developed. The addition of 2-amino-5-iodopyridine to 5 under reductive Heck conditions provided 7-tert-butoxycarbonyl-2-exo-(2′-amino-5′-pyridinyl)-7-azabicyclo [2.2.1]heptane (6). Compound 6 was the key intermediate used to prepare epibatidine analogues where the 2′-chloro group on the pyridine ring was replaced with a fluorine (1b), bromine (1c), iodine (1d), hydroxy (1e), amino (1f), dimethylamino (1g), trifluoromethanesulfonate (1h), and hydrogen (1i) group. (+)- and (-)-Epibatidine and compounds 1b-d and 1i all possess similar binding affinities at the (α4β2 nAChR receptors labeled by [3H]epibatidine. Compound 1f has affinity similar to nicotine, whereas compounds 1e, 1g, and 1h have much lower affinity. The binding affinity appears to be dependent upon the electronic nature of the substituent. However, other factors are also involved. None of the compounds possesses appreciable affinity for the α7 nAChR labeled by [125I] iodo-MLA. With the exception of 1f and 1g, all the epibatidine analogues are full agonists (tail flick test) in producing antinociception after intrathecal injection in mice.
Carroll,Liang,Navarro,Brieaddy,Abraham,Damaj,Martin
p. 2229 - 2237
(2007/10/03)

Synthesis of a fluorine-18 labeled derivative of epibatidine for in vivo nicotinic acetylcholine receptor PET imaging
Epibatidine (exo-2-(2'-chloro-5'-pyridyl)-7-azabicyclo[2.2.1]heptane), a natural compound isolated from the skin of the Ecuadorian poison frog Epipedobates tricolor, is the most potent nicotinic acetylcholine receptor (nAChR) agonist reported to date. In order to visualize and quantify in vivo these receptors in human brain using Positron Emission Tomography (PET), [18F]norchlorofluoroepibatidine (exo-2-(2'-[18F]fluoro-5'-pyridyl)-7-azabicyclo[2.2.1]heptane), a fluorine-18 (t(1/2): 110min) radiolabeled derivative of epibatidine has been designed. The corresponding 2'-bromo-, 2'-iodo- and 2'-nitro exo-2-(5'-pyridyl)-7-azabicyclo[2.2.1]heptane analogues as labeling precursors, as well as norchlorofluoroepibatidine as a reference compound have been synthesized by reductive, stereoselective, palladium-catalyzed Heck-type coupling between an N-Boc protected azanorbornene and the corresponding halopyridine. [18F]Norchlorofluoroepibatidine has been radiolabeled with fluorine-18 by nucleophilic aromatic substitution from the corresponding Boc-protected halo- and nitro precursors using [18F]FK-K222 complex in DMSO by conventional heating (at 150-180°C for 10min) or microwave activations (at 100 Watt, for 1 to 2.5min), followed by TFA-removal of the protective group. Typically, using the microwave activation procedure, 60-80mCi (2.22-2.96 GBq) of pure [18F]norchlorofluoroepibatidine could be obtained in less than 2h (110-115min) from the bromo labeling precursor, with specific radioactivities of 1.5-2.5Ci/μmol (55.5-92.5GBq/μmol) calculated for End of Bombardment. The preliminary PET experiments in baboon (Papio papio) with [18F]norchlorofluoroepibatidine show a high uptake and a rapid accumulation of the radiotracer into the brain within 30min. In the thalamus, a nAChR rich area, uptake of radioactivity reached a maximum at 40min (10% I.D./100mL tissue). The ratio of radioactivity thalamus/cerebellum (the latter being a nAChR poor area) was 2 at 40min and increased with time, up to 4.3 at 160min. Its specific regiodistribution and its high ratio of specific-to-nonspecific binding confirm the ideal profile of [18F]norchlorofluoroepibatidine as a suitable radioligand for PET imaging of nAChRs in the brain. Copyright (C) 1999 Elsevier Science Ltd.
Dolci, Lilian,Dolle, Frederic,Valette, Heric,Vaufrey, Francoise,Fuseau, Chantal,Bottlaender, Michel,Crouzel, Christian
p. 467 - 479
(2007/10/03)

New aza-thioxanthones: Synthesis and cytotoxicity
A new series of aza-thioxanthones has been synthesized and tested for in vitro cytotoxicity in a number of cell lines. Almost all the compounds were found to exhibit significant cytotoxicity in the leukemic MOLT-4 line, whereas some of them showed pronounced activity in the non-small lung cancer cell line HOP-92.
Varvaresou,Tsotinis,Papadaki-Valiraki,Siatra-Papastaikoudi
p. 861 - 864
(2007/10/03)

Synthesis and structure elucidation of new cytotoxic azathioxanthones
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Varvaresou,Tsotinis,Papadaki-Valiraki,Siatra-Papastaikoudi
p. 917 - 921
(2007/10/03)

Halogenation of pyridinium-N-(2'-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines
The regioselective halogenation of pyridinium-N-(2'-pyridyl)aminide 1 with N-chloro, bromo or iodosuccinimide under mild conditions is described. The method, combined with a reduction of the N-N bond, allows an easy preparation of 5-halo and 3,5-dihalo-2-aminopyridines 4.
Burgos,Delgado,Garcia-Navio,Izquierdo,Alvarez-Builla
p. 8649 - 8654
(2007/10/02)

Syntheses of two pyridine C-nucleosides as 'deletion-modified' analogues of dT and dC
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Hsieh,McLaughlin
p. 5356 - 5359
(2007/10/02)

A Total Synthesis of (+/-)-Epibatidine
A total synthesis of the potent non-opiate analgesic alcaloid epibatidine is described, in which the key step is reductive palladium-catalysed Heck-type coupling.The synthesis is concise (two steps from known compounds), highly convergent, and completely sttereoselective for the desired exo-isomer. - Key Words: Epibatidine, Analgesic, Alkaloid, Palladium-catalysed Coupling
Clayton, Simon C.,Regan, Andrew C.
p. 7493 - 7496
(2007/10/02)

Pyridinium-N-(2-pyridyl)aminides: A selective approach to substituted 2-aminopyridines
Differently substituted 2-aminopyridines have been prepared in two steps from pyridinium-N-(2-pyridyl)aminide.
Carceller, Rosa,Garcia-Navio, Jose L.,Izquierdo, Maria L.,Alvarez-Builla, Julio
p. 2019 - 2020
(2007/10/02)

Preparation and Properties of Pyridine-Analogue of TCNQ Dianion Salt
Bis(tetrapropyl- and tetrabutylammonium) 1,1'-(2,5-pyridinediyl)bis (4a and 4b) were prepared in order to investigate the properties of pyridine-analogue 3 of TCNQ as a new electron acceptor and its complexation with TTF.Although 3 was not isolated, the cyclic voltammetry of the salt 4 indicated that 3 was a stronger electron acceptor than TCNQ.The charge-transfer complex of TTF and 3 was prepared by mixing TTF with 3 which was generated in situ from electrolytic oxidation of 4 or from the oxidation of 2,5-bis(dicyanomethyl)pyridine, a precursor of 4, with hydrogen peroxide.It consisted of 1:1 composition of donor and acceptor and showed a high electrical conductivity of 19 Scm-1.The 2:1 complex was prepared by metathesis of (TTF)3(BF4)2 and 4, and also highly conductive.
Hama, Yoshiyuki,Nobuhara, Yukikazu,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
p. 1683 - 1687
(2007/10/02)

IODINATION OF SOME DIAZINES AND DIAZINE N-OXIDES
A number of monosubstituted pyrazines, pyrimidines, and their N-oxides having the electron-donating amino groups were successfully iodinated.Depending on the reaction conditions, the 3-substituted pyrazine 1-oxides having a bulky dialkylamino group yielded the 6-iodo and 2,6-diiodopyrazine N-oxide derivatives together with some deoxygenated products.The mechanism with supportive evidence was presented to account for these chemical transformations.
Jovanovic, Misa V.
p. 1195 - 1210
(2007/10/02)

Certain 6-substituted-2-pyridinamines
Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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(2008/06/13)

Substituted imidazolo-pyridines and method
Imidazolo-pyridine derivatives are provided having the structure STR1 wherein R is lower alkyl, lower alkenylalkyl, lower alkynylalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl or phenylalkyl and R1 is lower alkyl, phenylalkyl or di-lower alkylaminoalkyl and n is 0, 1 or 2. These compounds are useful as anthelmintic agents administered orally or parenterally.
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(2008/06/13)

Substituted imidazo [1,2-a] pyridines
Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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(2008/06/13)

Certain substituted imidazo [1,2-a] pyridines
Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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(2008/06/13)

Methyl 6-(phenylsulfinyl)imidazo[1,2-a]pyridine-2-carbamate, a potent, new anthelmintic
A series of methyl imidazo[1,2-a]pyridine-2-carbamates was synthesized for anthelmintic testing. The preparation of this class of compounds was simplified by utilization of a novel one-step condensation of the appropriately substituted 2-aminopyridine with methyl chloroacetylcarbamate. The most potent compound, methyl 6-(phenylsulfinyl) imidazo[1,2-a] pyridine-2-carbamate, was orally effective against a broad range of helminths in sheep and cattle, at a dosage of 2.5 mg/kg. Limited trials in swine and dogs demonstrated anthelmintic activity at higher dosages. Limited observations in sheep and cattle indicated that, in both species, a single oral dose of 200 mg/kg was well tolerated.
Bochis,Dybas,Eskola,Kulsa,Linn,Lusi,Meitzner,Milkowski,Mrozik,Olen,Peterson,Tolman,Wagner,Waksmunski,Egerton,Ostlind
p. 235 - 237
(2007/10/04)