Synthesis and bioactivities of heterocyclic lipids as PAF antagonists. 2

Chung, SK; Ban, Shurong; Kim, S.H.; Kim, B.E.; Woo, Soon Hyung; Summers, James Bradley; Conway, Richard G.

doi:10.1016/0960-894x(95)00174-r

Cited by 4 publications

(2 citation statements)

References 15 publications

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“…Interestingly, trans-and terminal epoxides gave only the THF product. Additionally, stoichiometric tributyltin methoxide was used by Chung et al 143 in 1996 for ring opening of a terminal epoxide by a hydroxy group to give 4-[(benzyloxy)methyl]oxetan-2-ylmethanol in 32% yield. Subsequently, Carreira and co-workers 69 used this methodology for synthesis of a bridged bicyclic morpholine; it was also used elsewhere.…”

Section: Cyclization Through C−o Bond Formationmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Section: Cyclization Through C−o Bond Formationmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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“…Likewise, they represent ak ey pharmacophore in artificial sweeteners, such as alitame. [90][91][92] The reported synthesis utilized Baylis-Hillman alcohols 62 and O,O-diethyl hydrogen phosphorodithioates 64 as substrates and involved the concomitant generation of an ucleophile,f ollowed by thia-Michael addition and intramolecular cyclization to access the resultant 2,3-disubstituted thietanes (65). Furthermore, to enhance the generality of this method, the authors performed the oxidation of Baylis-Hillman alcohols 62 into the corresponding aldehydes 63 by using oxidant IBX and subsequent thia-Michael addition with O,O-diethyl hydrogen phosphorodithioates 64,f ollowed by anion-induced cyclization with at ask-specific ionic liquid [bmim][XÀY],a fforded 2,3,4-trisubstituted thietanes 66 in excellent yields.…”

Section: Scheme29 K 3 Po 4 -Mediated Thia-michael Addition Reactionmentioning

confidence: 99%

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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Anticoagulants, Antithrombotics, and Hemostatics

Bisacchi

2003

Burger's Medicinal Chemistry and Drug Discovery

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Maintenance of proper blood flow is a complex and highly regulated physiological process, with multiple complementary and opposing mechanisms of control. Imbalances in these mechanisms can lead to a variety of pathological consequences, such as hemorrhage or obstructive clot (thrombus) formation in veins or arteries, leading to stroke, pulmonary embolism, heart attack, and other serious conditions. One of the overriding challenges with current or future drug strategies for antithrombotic, thrombolytic (clot dissolving), and hemostatic therapy is the precise correction of the pathologic imbalance without overcompensating and thus creating safety issues. Unfractionated heparin is widely used as an anticoagulant, but is being replaced in many of its applications by currently available alternative parenteral agents such as the low molecular weight heparins and the direct thrombin inhibitors. These efficacious alternative agents offer advantages in terms of more predictable pharmacokinetics and improved safety, thereby reducing or eliminating the need for patient monitoring and reducing or eliminating the risk of heparin‐induced thrombocytopenia. Orally bioavailable direct thrombin and/or Factor Xa inhibitors now under development seem poised to become available over the next several years and will represent viable alternatives to both the parenteral anticoagulants and to warfarin, the only currently available oral anticoagulant. These agents promise the convenience of an oral drug without the need of intensive patient monitoring, as warfarin requires. Other therapeutic targets under current investigation for anticoagulation include Factor VIIa and Factor IXa. Antiplatelet agents such as aspirin, clopidogrel, and the parenteral GPIIb/IIIa antagonists are valuable and widely used drugs. New antiplatelet agents that act by already validated mechanisms (e.g., P2Y 12 receptor antagonism) or that act by mechanisms not targeted by current agents will also likely emerge in the not too distant future. Newer clot‐selective fibrinolytics have advantages over older agents such as streptokinase. Fibrinolytic agents still in development may offer further improvements in terms of safety and longer plasma half‐life.

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Synthesis and bioactivities of heterocyclic lipids as PAF antagonists. 2

Cited by 4 publications

References 15 publications

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

Anticoagulants, Antithrombotics, and Hemostatics

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