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Journal articles on the topic 'Imidazo[1,2-b]pyrazoles'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Driowya, Mohsine, Hassan Allouchi, José Manuel Gally, Pascal Bonnet, and Gérald Guillaumet. "Synthesis of novel series of 7,7′-(substituted methylene)bis-imidazo[1,2-b]pyrazoles via an acid catalyzed one-pot three-component reaction." New Journal of Chemistry 42, no. 8 (2018): 5728–41. http://dx.doi.org/10.1039/c7nj05088g.

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An efficient and rapid synthesis of new series of N-alkyl-2-aryl-5H-imidazo[1,2-b]pyrazoles has been achieved in high yields through a three-component reaction of 3-amino-4-substituted pyrazoles, aromatic aldehydes and isocyanides mediated by acid catalysts.

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2

Demjén, András, Márió Gyuris, János Wölfling, László G. Puskás, and Iván Kanizsai. "Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach." Beilstein Journal of Organic Chemistry 10 (October 8, 2014): 2338–44. http://dx.doi.org/10.3762/bjoc.10.243.

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5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.

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3

Seneci, P., M. Nicola, M. Inglesi, E. Vanotti, and G. Resnati. "Synthesis of Mono- and Disubstituted 1H-Imidazo [1,2-B] Pyrazoles." Synthetic Communications 29, no. 2 (1999): 311–41. http://dx.doi.org/10.1080/00397919908085772.

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4

Sherif, Sherif M., Abdel-Haleem M. Hussein, and Yehya M. El-Kholy. "Novel synthesis of imidazo[1,2-b]pyrazoles and their fused derivatives." Archives of Pharmacal Research 17, no. 5 (1994): 298–303. http://dx.doi.org/10.1007/bf02974165.

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5

Seneci, P., M. Nicola, M. Inglesi, E. Vanotti, and G. Resnati. "ChemInform Abstract: Synthesis of Mono- and Disubstituted 1H-Imidazo[1,2-b]pyrazoles." ChemInform 30, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199924127.

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6

Barlin, GB, LP Davies, SJ Ireland, MML Ngu, and JK Zhang. "Imidazo[1,2-b]pyridazines. XII. Syntheses and Central Nervous System Activities of Some Substituted Imidazo[1,2-b]pyridazines and Related Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrimidines and Imidazo[1,2-a]pyrazines." Australian Journal of Chemistry 45, no. 5 (1992): 877. http://dx.doi.org/10.1071/ch9920877.

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Syntheses are reported for some 6-chloro(alkoxy,alkylthio and pheny1thio)-3-benzamidomethyl-(acetamidomethyl and methoxy)-2-arylimidazo[1,2-apyridines and some corresponding imidazo- [1,2- b]pyridazines, imidazo[1,2-a[pyrimidines and imidazo[l,2-a]pyrazines. IC50 values (or percentage displacement) are reported and discussed for the displacement of [3H]diazepam from rat brain membrane by each of these compounds. The imidazo[l,2-a[pyridines were generally slightly less potent than the imidazo[l,2- b]pyridazines but considerably more potent than the corresponding imidazo[1,2-a]pyrimidines or imi

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7

Aziz, Jessy, and Sandrine Piguel. "An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles." Synthesis 49, no. 20 (2017): 4562–85. http://dx.doi.org/10.1055/s-0036-1590859.

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This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.1 Introduction2 C–H Functionalization Reactions of N-Containing Heterocycles2.1 Imidazo[1,2-a]pyridines2.2 Pyrrolo[1,2-a]pyrazines2.3 Imidazo[1,2-b]pyrazoles2.4 Imidazo[1,2-a]pyrimidines2.5 Imidazo[1,2-a]py

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8

Goli, Shokoufe, Peiman Mirzaei, and Ayoob Bazgir. "One-pot sequential double annulations cascade reaction for imidazo[1,2-b]pyrazoles synthesis." Journal of the Iranian Chemical Society 15, no. 12 (2018): 2803–9. http://dx.doi.org/10.1007/s13738-018-1467-z.

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9

Rodrigues, Ingrid, Angelita M. Barcellos, Andrei L. Belladona, et al. "Oxone®-mediated direct arylselenylation of imidazo[2,1-b]thiazoles, imidazo[1,2-a]pyridines and 1H-pyrazoles." Tetrahedron 74, no. 31 (2018): 4242–46. http://dx.doi.org/10.1016/j.tet.2018.06.046.

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10

Grosse, Sandrine, Christelle Pillard, Stéphane Massip, et al. "Efficient Synthesis and First Regioselective C-3 Direct Arylation of Imidazo[1,2-b]pyrazoles." Chemistry - A European Journal 18, no. 47 (2012): 14943–47. http://dx.doi.org/10.1002/chem.201202593.

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11

Gambouz, Khadija, Mohsine Driowya, Mohammed Loubidi, et al. "Unusual rearrangement of imidazo[1,5-a]imidazoles and imidazo[1,2-b]pyrazoles into imidazo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines." RSC Advances 9, no. 50 (2019): 29051–55. http://dx.doi.org/10.1039/c9ra04609g.

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12

DaVies, Les P., Gordon B. Barlin, Stephen J. Ireland, and Maria M. L. Ngu. "Substituted imidazo[1,2-b]pyridazines." Biochemical Pharmacology 44, no. 8 (1992): 1555–61. http://dx.doi.org/10.1016/0006-2952(92)90472-u.

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13

Cui, Tao, Congxiang Li, Ming Li, and Lirong Wen. "Efficient Copper-Catalyzed Coupling Reaction for the Synthesis of Benzo[4,5]imidazo[1,2-b]pyrazoles." Chinese Journal of Organic Chemistry 37, no. 6 (2017): 1487. http://dx.doi.org/10.6023/cjoc201612029.

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14

Shawali, Ahmad Sami, Magda A. Abdallah, Mohamed R. Shehata, and Mohamed Kandil. "Synthesis and Tautomeric Structure of 3,7-bis(arylazo)-2,6-dimethyl-1H-imidazo[1,2-b]pyrazoles." Journal of Chemical Research 37, no. 3 (2013): 127–30. http://dx.doi.org/10.3184/174751913x13588723344455.

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15

GHOZLAN, S. S. "ChemInform Abstract: Synthesis of Some New Pyrazolo(1,5-a)pyrimidines and Imidazo(1,2-b) pyrazoles." ChemInform 23, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199220216.

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16

Schmitt, Martine, Jean-Jacques Bourguignon, Gordon B. Barlin, and Les P. Davies. "Imidazo[1,2-b]pyridazines. XXIV Syntheses of Some 3-(Variously Substituted) Imidazo[1,2-b] pyridazines, 6-Substituted 2-Benzoyl- imidazo[1,2-b]pyridazines and Pyrimido[1,2-b]pyridazin- 5-ium-3-olates and their Interaction with Central and Mitochondrial Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 8 (1997): 779. http://dx.doi.org/10.1071/c97030.

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The syntheses of some ethyl 2-{2′-aryl-6′-(chloro, iodo and methoxy)imidazo[1,2-b]pyridazin-3′-yl}-2-(acetoxy, acylamino, hydroxy and methoxy)acetates, 6-methyl-2-(p-tolyl)- and 6-chloro-2-(4′-chlorophenyl)-3-trimethylammoniomethylimidazo[1,2-b]pyridazine iodides (and reactions thereof), 2-benzoyl 6-substituted imidazo[1,2-b]pyridazines and 7-(methoxy, chloro and phenylthio)-2-phenylpyrimido-[1,2-b]pyridazin-5-ium-3-olates are reported. The ability of these compounds to displace [3H]diazepam from rat forebrain membrane [central benzodiazepine receptor (BZR)] and rat kidney membrane [mitochondr

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17

Farag, Ahmad M., and Kamal M. Dawood. "One-pot synthesis of imidazo[1,2-b]pyrazole, imidazo[1,2-b]-1,2,4-triazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[1,2-a]benzimidazole, and 1,2,4-triazolo[4,3-a]benzimidazole derivatives." Heteroatom Chemistry 8, no. 2 (1997): 129–33. http://dx.doi.org/10.1002/(sici)1098-1071(1997)8:2<129::aid-hc4>3.0.co;2-9.

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18

Barlin, Gordon B., Les P. Davies, and Peter W. Harrison. "Imidazo[1,2-b]pyridazines. XXI. Syntheses of some 3-Acylaminomethyl-6-(chloro and iodo)- 2-(substituted phenyl)-imidazo[1,2-b]pyridazines and -imidazo[1,2-a]pyridines and their Interaction with Central and Mitochondrial Benzodiazepine." Australian Journal of Chemistry 50, no. 1 (1997): 61. http://dx.doi.org/10.1071/c96130.

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A series of 3-acylaminomethyl-6-(chloro, iodo and methyl)-2-(phenyl, 4′-t-butylphenyl, 4′-cyclohexyl- phenyl, biphenyl-4′-yl, 4′-chlorophenyl and 4′-iodophenyl)imidazo[1,2-b]pyridazines and imidazo[1,2- a]pyridines has been prepared and examined for interaction with central and mitochondrial (peripheral- type) benzodiazepine receptors. The imidazo[1,2-b]pyridazines were generally more selective for the mitochondrial receptors than the corresponding imidazo[1,2-a]pyridines. Of these compounds, 3- acetamidomethyl-2-(biphenyl-4′-yl)-6-chloroimidazo[1,2-b]pyridazine (9) proved to be the most selec

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19

Barlin, GB. "Imidazo[1,2-B]Pyridazines. I. Some 3-Alkoxy-6-Halogeno-2-Phenyl-(and 4′-Substituted Phenyl)Imidazo[1,2-B]Pyridazines and 3-Methoxy-2,6-Diphenylimidazo[1,2-B]Pyridazine." Australian Journal of Chemistry 39, no. 11 (1986): 1803. http://dx.doi.org/10.1071/ch9861803.

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A series of 3-alkoxy-6-halogeno-2-phenyl(and 4′-substituted phenyl) imidazo [1,2-b] pyridazines (1) and 3-methoxy-2,6- diphenylimidazo [1,2-b] pyridazine have been prepared from the relevant pyridazin-3-amines and arylglyoxals, followed by O- alkylation of the corresponding imidazo [1,2-b]pyridazin-3(5H)-ones with diazoalkanes. 6- Chloro-3-methoxy-2-phenylimidazo[2,1-a] phthal-azine was prepared similarly.

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20

Grosse, Sandrine, Véronique Mathieu, Christelle Pillard, et al. "New imidazo[1,2-b]pyrazoles as anticancer agents: Synthesis, biological evaluation and structure activity relationship analysis." European Journal of Medicinal Chemistry 84 (September 2014): 718–30. http://dx.doi.org/10.1016/j.ejmech.2014.07.057.

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21

Grosse, Sandrine, Christelle Pillard, Stephane Massip, et al. "ChemInform Abstract: Efficient Synthesis and First Regioselective C-3 Direct Arylation of Imidazo[1,2-b]pyrazoles." ChemInform 44, no. 14 (2013): no. http://dx.doi.org/10.1002/chin.201314137.

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22

Barlin, GB, LP Davies, B. Glenn, PW Harrison, and SJ Ireland. "Imidazo[1,2-b]pyridazines. XV. Synthesis and Anxiolytic Activity of Some 3-(Benzamidomethyl and fluorobenzamidomethyl)-6-(fluoro, chloro and methylthio)-2-(4-tolyl and 3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 4 (1994): 609. http://dx.doi.org/10.1071/ch9940609.

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Syntheses are reported for some 3-( benzamido-and fluorobenzamido -methyl)-6-( fluoro , chloro and methylthio )-2(4-methyl-, 4-t-butyl-, 4-cyclohexyl- and 3,4-methylenedioxy-phenyl) imidazo-[1,2-b] pyridazines from the relevant 3-unsubstituted imidazo [1,2-b] pyridazines and the N-( hydroxymethyl ) benzamides. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(3- or 4-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl)-6-methylthioimidazo[1,2-b]- pyridazine bound most strongly, with IC50 2nM; but in behavioural tests in rats the most active compound

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23

N. Al-Mohammed, Nassir, Yatimah Alias, Zanariah Abdullah, and Hamid Khaledi. "Imidazo[1,2-b]isoquinoline-5,10-dione." Acta Crystallographica Section E Structure Reports Online 67, no. 7 (2011): o1666. http://dx.doi.org/10.1107/s1600536811022082.

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24

BARLIN, G. B., L. P. DAVIES, S. J. IRELAND, M. M. L. NGU, and J. ZHANG. "ChemInform Abstract: Imidazo(1,2-b)pyridazines. Part 12. Syntheses and Central Nervous System Activities of Some Substituted Imidazo(1,2-b)pyridazines and Related Imidazo(1,2-a)pyridines, Imidazo(1,2-a)pyrimidines and Imidazo( 1,2-a)pyrazines." ChemInform 23, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199234175.

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25

Barlin, GB, LP Davies, and PW Harrison. "Imidazo[1,2-b]Pyridazines. XVIII. Syntheses and Central Nervous System Activities of Some 6-, 7- and 8-(Chloro and methoxy)imidazo[1,2-a]pyridine Analogs." Australian Journal of Chemistry 48, no. 5 (1995): 1031. http://dx.doi.org/10.1071/ch9951031.

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Syntheses are reported for some 2-aryl-3-(benzamidomethyl and methoxy)-6(7 and 8)-chloro- and 6(and 8)-methoxy-imidazo[1,2-a]pyridines. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, those with 6-chloro and 6-methoxy groups bound most strongly, and relatively small differences only were observed between corresponding imidazo[1,2-a]pyridines and imidazo[1,2-b]pyridazines.

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26

Meta, Elda, Chiara Brullo, Michele Tonelli, et al. "Pyrazole and imidazo[1,2-b]pyrazole Derivatives as New Potential Antituberculosis Agents." Medicinal Chemistry 15, no. 1 (2019): 17–27. http://dx.doi.org/10.2174/1573406414666180524084023.

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Background: We screened a large library of differently decorated imidazo-pyrazole and pyrazole derivatives as possible new antitubercular agents and this preliminary screening showed that many compounds are able to totally inhibit Mycobacterium growth (>90 %). Among the most active compounds, we selected some new possible hits based on their similarities and, at the same time, on their novelty with respect to the pipeline drugs. </P><P> Methods: In order to increase the potency and obtain more information about structure-activity relationship (SAR), we designed and synthesized t

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27

Shawali, Ahmad Sami, Magda A. Abdallah, Mohamed R. Shehata, and Mohamed Kandil. "ChemInform Abstract: Synthesis and Tautomeric Structure of 3,7-Bis(arylazo)-2,6-dimethyl-1H-imidazo[1,2-b]pyrazoles." ChemInform 44, no. 34 (2013): no. http://dx.doi.org/10.1002/chin.201334117.

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28

Al-Zaydi, Khadijah Mohamed, Mariam Abd Alha Al-Shiekh, and Ebtisam Abdel-Aziz Hafez. "Enaminonitriles in Heterocyclic Synthesis: New Routes for the Synthesis of Some Novel Azolo[1,5-a]pyrimidine, Pyrimido[1,2-a]benzimidazole, Pyrido[1,2-a]benimdazole, Pyrazolo[3,4-b]pyridine, Pyrazole and Pyrimidine Derivatives." Journal of Chemical Research 2000, no. 1 (2000): 13–15. http://dx.doi.org/10.3184/030823400103165716.

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29

FARAG, A. M., and K. M. DAWOOD. "ChemInform Abstract: One-Pot Synthesis of Imidazo[1,2-b]pyrazole (IIIa), Imidazo[1,2-b]-1,2,4-triazole (IIIb), Imidazo[1,2-a]pyridine (Va), Imidazo[1,2-a]pyrimidine (Vb), Imidazo[1,2-a]benzimidazole (IX), and 1,2,4-Triazolo[4,3-a]benzimidazole (VII) Deriv." ChemInform 28, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199731068.

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30

Guillaumet, Gérald, Sandrine Grosse, Christelle Pillard, and Philippe Bernard. "Efficient C-7 or C-3/C-7 Direct Arylation of Tri- or Disubstituted Imidazo[1,2-b]pyrazoles." Synlett 24, no. 16 (2013): 2095–101. http://dx.doi.org/10.1055/s-0033-1339657.

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31

Barlin, GB, LP Davies, PW Harrison, NW Jacobsen, and AC Willis. "Imidazo[1,2-b]Pyridazines. XVI. Synthesis and Central Nervous System Activities of Some 6-(Chloro, Alkylthio, Phenylthio, Benzylthio or Pyridinylmethylthio)-3-(unsubstituted, benzamidomethyl or methoxy)-2-(styryl or benzoyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 11 (1994): 1989. http://dx.doi.org/10.1071/ch9941989.

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Some 6-( chloro, alkylthio, phenylthio, benzylthio or pyridinylmethylthio )-3-( unsubstituted , benzamidomethyl or methoxy )-2-styrylimidazo[1,2-b] pyridazines and 6-chloro-3-( unsubstituted and benzamidomethyl )-2-benzoylimidazo[1,2-b] pyridazines have been prepared and tested for their ability to displace [3H]diazepam from rat brain plasma membranes. The structures of 6-chloro-2-benzoyl[and 6-fluoro-2-(4′-tolyl)] imidazo [1,2-b] pyridazine have been confirmed by X-ray analyses. The reactions of 6-methylthio(and 6-phenylthio)pyridazin-3-amines with 3-bromo-1-phenylpropane-1,2-dione also have

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32

Barlin, Gordon B., Les P. Davies, Stephen J. Ireland, and Maria M. L. Ngu-Schwemlein. "Imidazo[1,2-b]pyridazines. XXII. Syntheses of Some 2-Aryl-3-methoxy-6-(pyridinylmethylthio and pyridinylmethylamino)imidazo[1,2-b]pyridazines and Their Interaction with Central and Mitochondrial (Peripheral-Type) Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 2 (1997): 91. http://dx.doi.org/10.1071/c96136.

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2-Aryl-3-methoxy-6-(pyridinylmethylthio and pyridinylmethylamino)imidazo[1,2-b]pyridazines have been prepared and examined as ligands for benzodiazepine receptors. Most were highly effective in displacing [3H]diazepam from central benzodiazepine receptors present in rat brain membranes but showed little capacity for its displacement from mitochondrial (peripheral-type) benzodiazepine receptors present in rat kidney membranes. For example, 3-methoxy-2-(3′,4′-methylenedioxyphenyl)-6-(pyridin-2′′-ylmethylthio)imidazo[1,2-b]pyridazine had an IC50 value of 1 · 7 nM for central receptors but gave on

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33

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XIV. Syntheses and Central Nervous System Activities of Some 6-(Methoxy-, dimethoxy-, methylenedioxy-, chloro- and fluoro-)-3-alkoxy-2-phenyl(and substituted phenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 46, no. 3 (1993): 353. http://dx.doi.org/10.1071/ch9930353.

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Syntheses are reported for 28 new 3-alkoxy-6-(3′-methoxy-,3′,4′-dimethoxy, 3′,4′-methylene-dioxy-, 2′- and 4′-chloro- and 4′-fluoro-benzylamino)-2-phenyl(and substituted phenyl) imidazo -[1,2-b] pyridazines from the corresponding 6-substituted pyridazin-3-amine 2-oxides with α- bromoacetophenones, followed by alkylation of the intermediate 3-hydroxyimidazo[1,2-b] pyridazines. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(2′-ethoxyethoxy)-6(3′-methoxybenzylamino)-2-phenyl- and 6(3′,4′-methylenedioxybenzylamino )-2-(3″,4″-methylenedioxyphenyl)-3-

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34

Galeta, Juraj, Lukáš Tenora, Stanislav Man, and Milan Potáček. "Dihydropyrrolo[1,2-b]pyrazoles: withasomnine and related compounds." Tetrahedron 69, no. 34 (2013): 7139–46. http://dx.doi.org/10.1016/j.tet.2013.06.009.

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35

Saldabol, N. O., J. Popelis, and V. A. Slavinskaya. "ChemInform Abstract: Formylation of Furyl-Substituted Imidazo[1,2-a]pyridine, Imidazo[1,2-a]pyrimidine and Imidazo[2,1-b]thiazole." ChemInform 33, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200218074.

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36

Delaye, Pierre-Olivier, Mélanie Pénichon, Leslie Boudesocque-Delaye, Cécile Enguehard-Gueiffier, and Alain Gueiffier. "Natural Deep Eutectic Solvents as Sustainable Solvents for Suzuki–Miyaura Cross-Coupling Reactions Applied to Imidazo-Fused Heterocycles." SynOpen 02, no. 04 (2018): 0306–11. http://dx.doi.org/10.1055/s-0037-1610400.

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Herein, we present the first Suzuki–Miyaura cross-coupling in a sustainable natural deep eutectic solvent (NaDES) applied to biologically relevant imidazo-fused scaffolds imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine. The choline chloride/glycerol (1:2, mol/mol) NaDES allowed the functionalisation of diverse positions on the heterocycles with various boronic acids, by using 2.5 mol% of readily available Pd(OAc)2. Notably, the catalytic system proceeds without any ligands or additives, without protection from the atmosphere.

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37

Soltani, Siavash Salek, S. Morteza F. Farnia, and Alireza Foroumadi. "Synthesis and Antibacterial Activity of New Chalcones Bearing an Imidazo[ 1,2-a]pyridine Moiety." Current Chemical Biology 15, no. 2 (2021): 163–70. http://dx.doi.org/10.2174/2212796815666210223110208.

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Aim and Objective: Herein, A series of new imidazo[1,2-a]pyridine-chalcone derivatives 3a-m were designed and synthesized to find a new class of antibacterial agents. These compounds were prepared by the aldol condensation of 2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde 2a-b with acetophenone derivatives and other aromatic acetyls. High reaction yields were obtained in a short reaction time, through applying this multi-step pathway. Materials and Methods: In vitro antibacterial activities of the synthesized imidazo[1,2-a]pyridinechalcones were measured against S. aureus, B. subtilis and E. co

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38

Hauptmann, Siegfried, Horst Wilde, and Matthias Szymanowski. "Synthese und Farbstoffbildung von Benzo [1,2-b:5,4-b']bis(1H-imidazo[1,2-b]pyrazolen)." Zeitschrift für Chemie 28, no. 12 (2010): 441–42. http://dx.doi.org/10.1002/zfch.19880281211.

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39

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-B]Pyridazines. III. Syntheses and Central Nervous-System Activities of Some 6-Chloro-3-methoxy (and ethoxy)-2-aryl (and heteroaryl)imidazo[1,2-B]pyridazines." Australian Journal of Chemistry 41, no. 8 (1988): 1149. http://dx.doi.org/10.1071/ch9881149.

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The synthesis of a series of 6-chloro-3-methoxy(and ethoxy )-2- phenyl[and (variously substituted phenyl), thienyl, and naphthalenyl ] imidazo [1,2-b] pyridazines and a 6-fluoro analogue are reported. These compounds were tested for their ability to displace [3H]diazepam bound to washed rat brain plasma membranes. Under standard assay conditions (see Experimental) and in the presence of 100 μM γ- aminobutyric acid, 6-chloro-3-methoxy-2-(p-tolyl ) imidazo [1,2- b] pyridazine was the most active compound with an IC50 value of 148 nM (cf. diazepam, with IC50 of 4.2 nM).

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40

Kutrov, G. P., N. V. Kovalenko, and Yu M. Volovenko. "Synthesis and properties of cyanomethyl derivatives of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, and imidazo[2,1-b]thiazole." Russian Journal of Organic Chemistry 44, no. 2 (2008): 257–62. http://dx.doi.org/10.1134/s1070428008020127.

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M., Sumakanth, V. Malla Reddy, V. S. H. Krishnan, and B. S. Sastry. "Synthesis of Some New Imidazo[1,2-b] Pyridazines." International Journal of Pharmaceutical Sciences and Nanotechnology 2, no. 1 (2009): 471–76. http://dx.doi.org/10.37285/ijpsn.2009.2.1.14.

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Several 2,6-diaryl-imidazo[1,2-b]pyridazines (5 & 7) were prepared from 3-amino-6-aryl-pyridazines (3) which in turn were obtained from the corresponding 6-aryl-pyridazine-3(2H)-ones(1) via., 6-aryl-pyridazin-3(2H)-thiones (2) as intermediates, by a reaction with an appropriate a-halocarbonyl compounds (4) or a-haloacyl carbamates (6) in a suitable solvent at reflux temperature. The resulted products were characterized by their physical, analytical and spectral data.

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42

Barlin, GB, LP Davies, SJ Ireland, CLY Khoo, and TMT Nguyen. "Imidazo[1,2-B]pyridazines. IX. Syntheses and Central Nervous System Activities of Some 3-Alkoxy-6-(o-alkoxy, o-methylthio- or o-fluoro-phenoxy)-2-arylimidazo[1,2-b]pyridazines." Australian Journal of Chemistry 43, no. 3 (1990): 503. http://dx.doi.org/10.1071/ch9900503.

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Syntheses are reported for a series of 6-(o-methoxy -, o-ethoxy -, o-methylthio - and o-fluoro-phenoxy )-3-( methoxy and ethoxy )-2- phenyl(substituted phenyl and pyridin-3″-yl) imidazo [1,2-b] pyridazines . IC50 values are reported for the displacement of 3H-diazepam from rat brain membrane by each of these compounds. The most active compounds were found to be 3-ethoxy-2-(p- fluorophenyl )-6-(o- methoxyphenoxy )-, 3-methoxy-6-(o- methoxyphenoxy )-2-(m-nitrophenyl )- and 3-methoxy-6-(o- methoxyphenoxy )-2-(3″,4″-methylenedioxy ) imidazo [1,2-b] pyridazines with IC5O values of 15, 18 and 19 nM

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Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XIII. Syntheses and Central Nervous System Activities of Some 2-Benzyl(phenethyl, biphenyl-4'-yl, 6'-methylnaphthalen-2'-yl, t-Butyl and cyclohexyl)-3-methoxy(acylaminomethyl and dimethylaminomethyl)-6-(variously substituted)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 8 (1992): 1281. http://dx.doi.org/10.1071/ch9921281.

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6-(Variously substituted)-3-methoxy(unsubstituted, dimethylaminomethyl, acetamidomethyl and benzamidomethy1)-2-benzyl(phenethyl, biphenyl-4'-yl, 6'-methylnaphthalen-2'-yl, t-butyl and cyclohexyl)imidazo[1,2-b] pyridazines have been prepared and examined for activity in the central nervous system. Of these, 2-benzyl-3-methoxy-6-(3'-methoxybenzylamino) imidazo[1,2-b]pyridazine (IC50 88nM) bound most strongly to rat brain membrane. In general, the order of activity for groups at the 2-position was Ph > PhCH2 > PhCH2CH2 > C6H4Ph-p, 6'-methylnaphthalen-2'-yl, c-C6H11 or But.

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Maslov, Dmitry A., Kirill V. Shur, Aleksey A. Vatlin, and Valery N. Danilenko. "MmpS5-MmpL5 Transporters Provide Mycobacterium smegmatis Resistance to imidazo[1,2-b][1,2,4,5]tetrazines." Pathogens 9, no. 3 (2020): 166. http://dx.doi.org/10.3390/pathogens9030166.

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The emergence and spread of drug-resistant Mycobacterium tuberculosis strains (including MDR, XDR, and TDR) force scientists worldwide to search for new anti-tuberculosis drugs. We have previously reported a number of imidazo[1,2-b][1,2,4,5]tetrazines – putative inhibitors of mycobacterial eukaryotic-type serine-threonine protein-kinases, active against M. tuberculosis. Whole genomic sequences of spontaneous drug-resistant M. smegmatis mutants revealed four genes possibly involved in imidazo[1,2-b][1,2,4,5]tetrazines resistance; however, the exact mechanism of resistance remain unknown. We use

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Kuz'menok, N. M., and A. M. Zvonok. "Synthesis of 3-aryl-5-methylpyrrolidino[1,2 b]pyrazoles." Chemistry of Heterocyclic Compounds 30, no. 1 (1994): 44–46. http://dx.doi.org/10.1007/bf01164730.

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Grosse, Sandrine, Christelle Pillard, Philippe Bernard, and Gerald Guillaumet. "ChemInform Abstract: Efficient C-7 or C-3/C-7 Direct Arylation of Tri- or Disubstituted Imidazo[1,2-b]pyrazoles." ChemInform 45, no. 8 (2014): no. http://dx.doi.org/10.1002/chin.201408144.

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Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-b]Pyridazines. VIII. Syntheses and Central Nervous System Activities of Some 6-Benzylamino (and methoxybenzylamino)-3-methoxy-2-phenyl(Substituted phenyl or pyridinyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 10 (1989): 1759. http://dx.doi.org/10.1071/ch9891759.

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Syntheses and IC50 values for the displacement of 3H-diazepam from rat brain plasma membrane are reported for a series of 6-benzylamino(and methoxybenzylamino )-3-methoxy-2-phenyl(substituted phenyl and pyridinyl )imidazo[l,2-b]pyridazines (and their 6-anilino and 6-phenethylamino analogues). The results are compared with those reported previously (by us) for the 6-chloro, 6-phenoxy, 6-benzylthio, and 6-benzyloxy compounds. In the imidazo[l,2-b]pyridazine ring system, 6-(o- and m- methoxybenzylamino ) groups were found to be beneficial to binding activity; eight compounds have been prepared wi

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Iwata, Satoru, and Kiyoshi Tanaka. "Electrochemical properties of pyrido[1′,2′:1,2]imidazo[4,5-b]pyrazine and pyrido[1′,2′:1,2]imidazo[4,5-b]quinoxaline derivatives." Journal of Heterocyclic Chemistry 35, no. 4 (1998): 939–41. http://dx.doi.org/10.1002/jhet.5570350426.

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Roslan, Irwan Iskandar, Kian-Hong Ng, Stephan Jaenicke, and Gaik-Khuan Chuah. "Photocatalytic regeneration of brominating agent in the visible light-mediated synthesis of imidazo[1,2-a]pyridines." Catalysis Science & Technology 9, no. 6 (2019): 1528–34. http://dx.doi.org/10.1039/c9cy00141g.

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Rajesham, Bandari, Vemula Arunkumar, Praveen Kumar Naikawadi, and K. Shiva Kumar. "Copper-catalyzed cascade C–N coupling/C–H amination: one pot synthesis of imidazo[1,2-b]indazole." New Journal of Chemistry 44, no. 37 (2020): 15816–20. http://dx.doi.org/10.1039/d0nj03022h.

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