Synthesis and Anticonvulsant Activity of Some 7-Alkoxy-2H-1,4-benzothiazin-3(4H)-ones and 7-Alkoxy-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazines

Zhang, Liqiu; Guan, Liping; Wei, Cheng‐Xi; Deng, Xian‐Qing; Quan, Zhe‐Shan

doi:10.1248/cpb.58.326

Cited by 35 publications

(17 citation statements)

References 12 publications

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“…Compound 11 showed an ED 50 of 30.1 mg/kg (Table 1), TD 50 of 286 mg/kg, and PI of 9.5 which is greater than the reference drug carbamazepine with the PI value of 6.0 [21].…”

Section: The Quinoline Functional Groupmentioning

confidence: 90%

“…Their anticonvulsant activities were evaluated by the MES test and the sc-PTZ test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test with a median toxic dose (TD 50 ) value of 54.5 mg/kg, MES and sc-PTZ tests showed that compound 1 (Table 1) was the most potent of this series with an effective dose (ED 50 ) value of 11.8 and 6.7 mg/kg and protective index (PI = TD 50 /ED 50 ) value of 4.6 and 8.1, respectively [12]. …”

Section: The Quinoline Functional Groupmentioning

confidence: 99%

“…In the anti-MES test, compound 3 showed ED 50 of 12.3 mg/kg (Table 1), TD 50 of 547.5 mg/kg, and the PI of 44.5 which was much greater than the PI of the reference drugs phenytoin, phenobarbital, carbamazepin and valproate [14]. Sun et al, reported the synthesis of 8-alkoxy-4,5-dihydro- [1,2,4]triazole [4,3- 36.5 and 33.9 in the MES and sc-PTZ tests, respectively.…”

Section: The Quinoline Functional Groupmentioning

confidence: 99%

“…Pharmacological tests showed that compound 6 was the most active and also had the lowest toxicity (Table 1). In the anti-MES test, it showed ED 50 of 8.2 mg/kg, TD 50 of 318.3 mg/kg, and PI of 39.0 which was much greater than the PI of the reference drugs phenytoin and carbamazepine [16].…”

Section: The Quinoline Functional Groupmentioning

confidence: 99%

“…The most active compound 14 showed anti-MES activity with an ED 50 value of 14.3 mg/kg and TD 50 value of 434 mg/kg after i.p. injection to mice (Table 1), which showed compound 14 with a PI of 30.3 in the MES test [24].…”

Section: The Quinoline Functional Groupmentioning

confidence: 99%

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Current Research on Antiepileptic Compounds

2015

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Epilepsy affects about 1% of the world's population. Due to the fact all antiepileptic drugs (AEDs) have some undesirable side effects and about 30% of epileptic patients are not seizure-free with the existing AEDs, there is still an urgent need for the development of more effective and safer AEDs. Based on our research work on antiepileptic compounds and other references in recent years, this review covers the reported work on antiepileptic compounds which are classified according to their structures. This review summarized 244 significant anticonvulsant compounds which are classified by functional groups according to the animal model data, although there are some limitations in the data. This review highlights the properties of new compounds endowed with promising antiepileptic properties, which may be proven to be more effective and selective, and possibly free of unwanted side effects. The reviewed compounds represent an interesting possibility to overcome refractory seizures and to reduce the percentage of patients with a poor response to drug therapy.

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“…Compound 11 showed an ED 50 of 30.1 mg/kg (Table 1), TD 50 of 286 mg/kg, and PI of 9.5 which is greater than the reference drug carbamazepine with the PI value of 6.0 [21].…”

Section: The Quinoline Functional Groupmentioning

confidence: 90%

Section: The Quinoline Functional Groupmentioning

confidence: 99%

Section: The Quinoline Functional Groupmentioning

confidence: 99%

Section: The Quinoline Functional Groupmentioning

confidence: 99%

Section: The Quinoline Functional Groupmentioning

confidence: 99%

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Current Research on Antiepileptic Compounds

2015

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A Multicomponent Strategy for the Regioselective Synthesis of [1,3]‐Thiazinones from an Abundant Feedstock: Scope and Structural Elucidation

2016

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Anovel and regioselective protocol for the synthesis of [1,3]-thiazinones via multicomponent reactions of readily available isothiocyanates, hydrazine monohydrate, aldehydes and dialkyl acetylenedicarboxylates is described. This approach exhibitso perational simplicity,o fferinganew and expedient strategy for the direct synthesis of synthetically useful [1,3]-thiazinone compounds in good to excellent yields. The method could provide al ow-cost and environmentally benign alternative to currently employed methods. Moreover, unambiguous determination of the single product regioisomer throughd etailed 2D NMR spectroscopy,t he scope and limitations of this environmentally friendly dominor eactionare discussed.Supportinginformation for this article can be found under http:// dx.Scheme2.Four-component reaction of phenyl isothiocyanate 1a,h ydrazine monohydrate 2,b enzaldehyde 3a anddimethyl acetylenedicarboxylate (DMAD) 4a at RT.Scheme1.Substrate scope for the synthesis of (Z)-alkyl-3-((E)-alkyl/arylideneamino)-2-(alkyl/arylimino)-4-oxo-3,4-dihydro-2H-1,3-thiazine-6-carboxylate.

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Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

2018

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The thia-Michael addition reactionh as been demonstrated to be ah ighly powerful tool in organic synthesis. Indeed, the influential natureo ft his reactionh as been wellestablished in the fields of medicinal chemistry,c atalysis, drug discovery,a nd materials science. The emergence of numerous synthetic strategies that take advantage of thia-Michael addition reactions of electron-deficienta lkenes has unleashed countless opportunities for the design and synthesis of diverse biologically relevant organosulfurc ompounds. However,d espite myriad potential synthetic applications, there has not been anye xclusive reviewso ft he thia-Michael addition reaction. Therefore, this Focus Review plots the journeyo ft he thia-Michael addition reaction in organic synthesis, and is categorized according to catalyzed and catalyst-free thia-Michael addition reactions. Figure 1. Summary of the applicationsoft hia-Michael adducts.[a] Dr.Scheme1.Catalyzed pathways for the thia-Michael addition reaction.EW-G = electron-withdrawing group.Scheme2.Acetic-acid-catalyzed thia-Michael additionr eaction proposed by Allen et al. [24] AsianJ.O rg.Scheme3.Indium-bromide-catalyzed thia-Michael addition reaction.Scheme4.Thia-Michael addition reaction followed by a1 ,2-addition of TMSCN in one pot. TMSCN = trimethylsilyl cyanide.Scheme5.Bi III -catalyzedt hia-Michael additionreactiono fa,b-unsaturated carbonyl compounds. Tf = trifluoromethanesulfonyl.Scheme6.Bismuth-triflate-catalyzed synthesis of bis-thioether compounds. Bn = benzyl.Scheme7.Iron-/copper-catalyzed thia-Michael additionr eaction.Scheme8.VO(OTf) 2 -mediated synthesis of b-mercapto ketones. Np = naphthyl.Scheme9.Substrate scope for the synthesis of 3-sulfanyl-substituted 1-(arylamino)-pyrrolidine-2,5-diones.Scheme10. Regio-and enantioselective addition at the d position of conjugated systems.Scheme11. Mechanistic modelf or the enantioselective d addition of at hiol to an a,b,g,d-unsaturated dienone,catalyzed by achiral Fe III Àsalenc omplex.Scheme12. Chemoselectivesynthesis of 2-amino-3,1-benzothiazines (15) and 3,4-dihydroquinazoline-2-thiones (16)byu sing ortho-aminocinnamate (13)a nd isothiocyanates 14.Scheme13. Reactionmechanism for the chemoselective synthesis of 2amino-3,1-benzothiazines (15)and 3,4-dihydroquinazoline-2-thiones (16).Scheme14. ZrCl 4 -assisted three-component reactionf or the synthesiso fbaryl-b-mercapto ketones.Scheme15. LiF-nanocube-mediated thia-Michael addition reaction.Scheme57. Ni II -catalyzed enantioselective synthesiso f2-aryl-3-nitrothiochroman-4-ols.Scheme58. Te ntative reaction mechanism for the Ni II -catalyzed asymmetric synthesis of 2-aryl-3-nitrothiochroman-4-ols.Scheme59. Pepsin-catalyzed synthesis of functionalized chiral dihydrothiophenes.Scheme69. Mechanistic aspects of the stereoselectives ynthesis of tetrahydrothioxanthenones.Scheme70. Enantioselectivesynthesis of methyl 2-((R)-2-nitro-1-(aryl/heteroaryl)ethylthio)acetatesa nd thiomorpholin-3-ones.Scheme71. Water-accelerated thia-Michael additionr eaction proposedb y Chakraborti and co-work...

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Synthesis and Anticonvulsant Activity of Some 7-Alkoxy-2H-1,4-benzothiazin-3(4H)-ones and 7-Alkoxy-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazines

Cited by 35 publications

References 12 publications

Current Research on Antiepileptic Compounds

Current Research on Antiepileptic Compounds

A Multicomponent Strategy for the Regioselective Synthesis of [1,3]‐Thiazinones from an Abundant Feedstock: Scope and Structural Elucidation

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

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