Vasorelaxant Activity of Phthalazinones and Related Compounds.

Olmo, Esther del; Barboza, Bianca; Ybarra, María Inés; López-Pérez, Jose Luis; Carrón, Rosalı́a; Sevilla, María A.; Boselli, Cinthia; Feliciano, Arturo San

doi:10.1002/chin.200633164

Cited by 10 publications

(10 citation statements)

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“…Some phthalazinones attained, the total relaxation of the organ at micromolar concentrations. For the most potent compound (EC50=0.43microM) the affinities for α1A, α1B and α1D adrenergic sub-receptors were determined (del Olmo et al, 2006). Discovery of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors based on a phthalazinone scaffold.…”

Section: Azelastinmentioning

confidence: 99%

Pharmacological activities of various phthalazine and phthalazinone derivatives

Int¹

2019

Preprint

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Various pthalazine derivatives have been synthesized and tested for their diverse biological activities. Pthalazine derivatives have been exhibited pharmacological activities like antitumor, PARP-1 inhibitors, antimicrobial, antivirus, antihistamine-H1, antiallergic rhinitis, antifungal, anti-inflammatory, anti-proliferative, COX-2 inhibitor, LOX-5 inhibitor, antidiabetes, and other biological activities like imaging agent. Pthalazine derivatives were also used as agrochemicals and chemicals. Various synthetic aspects indicate that pthalazines derivatives are easy to synthesize which can produce a wide variety of activity.

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Section: Azelastinmentioning

confidence: 99%

Pharmacological activities of various phthalazine and phthalazinone derivatives

Int¹

2019

Preprint

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“…Phthalazinones 5,7-9 were synthesized from commercially available phthalic anhydride in 2-3 steps as depicted in (Scheme 1 and 2) [45][46][47][48][49][50][51].…”

Section: Synthesis Of Phthalazine Derivatives From Hydrazine and Hydrmentioning

confidence: 99%

Recent Developments in Chemistry of Phthalazines

El-Azm¹,

Mahmoud²,

Hekal³

2014

Organic Chem Curr Res

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El-Azm et al., Organic Chem Curr Res 2015, 4:1 http://dx.Hydrazines with 2-acyl benzoic acids: Kirill et al. [31] reported the cyclization of 2-nitro-5-chloro phenylhydrazine27 with acyl benzoic acids 28 yielded 2-(2-nitro-5-chlorobenzene)-4-substituted phthalazin-1-ones 29 (Scheme 7).Lukacs and Simig [61] adopted a novel method for the synthesis of phthalazine derivatives 32 via the reaction of benzophenones30 with chromium (VI) oxide in a mixture of acetic anhydride and sulphuric acid followed by cyclization of the products with hydrazine hydrate in refluxing ethanol (Scheme 8).Hydrazine with 1,2-diester:The dimethylphthalate derivative 33 reacted with hydrazine to yield the desired phthalhydrazide34 which undergo chlorination with phosphorus oxychloride to give 35. Subsequent treatment with sodium methoxide afforded the methoxychloride 36 [62] (Scheme 9). Hydrazines with Phthalides: Chloroformylation of 3-methoxy benzoic acid 37 and subsequently radical bromination of 38 produced 39 in good yield. Treatment with triphenyl phosphine gave 40 and wittig olefination with 3,5-dichloro-4-pyridine carboxaldehyde 41 afforded the phthalide 42. Hydrazine cyclization of 42 resulted phthalazine derivative 43 [42] (Scheme 10). Cockcroft et al. [12] synthesized the phthalazinone derivative 47 according the following (Scheme 11). AbstractThis review highlights the methods used for the synthesis of phthalazine derivatives and fused phthalazinones. Their reactivity and synthetic importance were investigated. Phthalazine derivatives can be used as building blocks for heterocycles as well as fused heterocyclic compounds. Scheme 1: Synthesis of phthalazinone derivatives 2 and 5 Scheme 2: Synthesis of phthalazinone derivatives 7-9. Reagents and conditions: (a) CHCl 3 , reflux, 5 h, 51%; (b) hydrazinehydrate, EtOH, addition at rt and then reflux, 90˚C, 2 h, 71%; (c) MeI, KOBu t , DMF, 30 min, 80%; (d) LiOH, THF:MeOH:water (1:1:1), rt, 8-10 h, 81%. Scheme 3: Synthesis of phthalazin(2H)-1-one 11, 12 Scheme 4: Synthesis of 2-[1-(4-oxo-3,4-dihydrophthalazin-1-yl)alkyl]-1Hisoindole-1,3-(2H)-diones Scheme 5: Synthesis of 1,4-disubstituted phthalazinylpiperazine derivatives 21 Scheme 6: One-pot Synthesis of thiadiazinyl-phthalazine-1,4-diones 24 and 26 Scheme 7: Synthesis of 4-substituted phthalazin-1-ones 29. Scheme 8: Synthesis of phthalazine derivatives 32 Scheme 9: Hydrazinolysis of dimethylphthalate derivative 33 Citation: El-Azm FSMA, Mahmoud MR, Hekal MH (2015) Recent Developments in Chemistry of Phthalazines. Organic Chem Curr Res 1:132. Scheme 23: Synthesis of 1H-pyrazolo [1,2-b] phthalazin-5,10-dione derivatives 92 Scheme 24: A plausible mechanism for the synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones 95 Scheme 25: Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives 97. Scheme 28: Synthesis of 1-{[(1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1Hpyrazolo[1,2-b] phthalazine-5,10-dione derivatives 104 Scheme 30: Synthesis of 2H-indazolo[1,2-b] phthalazine-triones 107 Scheme 29: Synthesis of 2H-indazolo[2,1-b]pht...

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“…Pyrrolopyrimidines have a wide range of applications in medicinal chemistry; they show antimicrobial, antitumor, antiasthmatic, antihypertensive, and anti‐inflammatory activities. Pyrimidoisoindoles show high vasorelaxtant,[26a] antiplasmodial,[26b] and antifungal actions. The spiroquinazolinone, spiropiperidine, and spiroadamantane skeletons, in turn, are known to have a wide range of pharmacological properties, including antimalarial and anti‐influenza activities .…”

Section: Introductionmentioning

confidence: 99%

Continuous‐Flow retro‐Diels–Alder Reaction: A Process Window for Designing Heterocyclic Scaffolds

et al. 2018

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The synthesis of racemic and enantiopure tricyclic and tetracyclic pyrrolopyrimidinones, pyrimidoisoindoles, and spiropyrimidinones, as valuable new chemical entities (NCE), based on a highly controlled continuous‐flow (CF) retro‐Diels–Alder protocol is presented. This approach ensures enhanced safety, and gave the target pyrimidinone derivatives 17–25 in yields higher than those obtained in batch and microwave processes. These results were achieved through careful optimization of the reaction parameters. We also developed an alternative time‐efficient route for the synthesis of intermediate quinazolinones 2–16 involving a three‐step domino ring‐closure reaction followed by spirocyclization under continuous‐flow conditions, starting from β‐aminonorbornene carboxamides 1a–1d and γ‐keto acids or cycloalkanones.

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Vasorelaxant Activity of Phthalazinones and Related Compounds.

Cited by 10 publications

References 1 publication

Pharmacological activities of various phthalazine and phthalazinone derivatives

Pharmacological activities of various phthalazine and phthalazinone derivatives

Recent Developments in Chemistry of Phthalazines

Continuous‐Flow retro‐Diels–Alder Reaction: A Process Window for Designing Heterocyclic Scaffolds

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