Phosphine-Catalyzed Construction of Sulfur Heterocycles

Gabillet, Sandra; Lecerclé, Delphine; Loreau, Olivier; Carboni, Michaël; Dézard, Sophie; Gomis, Jean-Marie; Taran, Frédéric

doi:10.1021/ol701563e

Cited by 78 publications

(30 citation statements)

References 18 publications

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“…The appearance of the ylidene proton of compounds 4a-c, 4f-h at δ= 7.78-7.86 confirmed the formation of Z-isomers. 9,15,[23][24][25][26][27][28] On the other hand, the ylidene proton of compounds 4d and 4i were revealed at δ= 8.00-8.16, slightly downfield shifted than the other synthesized analogues, which could be attributed to the anisotropic effect of the hydroxyl group oriented at the o-position of the arylidene function. Furthermore, reaction of 4-thiazolidinones 3a, b with formaldehyde and the appropriate heteroalicyclic amines (pyrrolidine, piperidine, morpholine and N-methylpiperazine) through Mannich reaction yielded 5a-h.…”

Section: Resultsmentioning

confidence: 92%

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Hanna

George

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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2-(5-Arylidene-4-oxo-3-phenyl-thiazolidin-2-ylidene)-3-oxo-propionitriles 4a-j were prepared via condensation of aromatic aldehydes with 4-thiazolidinones 3a, b. The latter was obtained via electrophilic attack of phenylisothiocyanate on 3-oxo-propionitriles 1a, b followed by reaction with chloroacetyl chloride under basic condition. Additionally, 2-(5-heteroalicyclic methylene) analogues 5a-h were prepared via Mannich reaction of the appropriate secondary amines and formaldehyde with 4-thiazolidinones 3a, b. Many of the synthesized compounds exhibited promising antitumor properties against colon HCT116 and breast T47D cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explain the observed antitumor properties.Key words thiazolidinone; quantitative structure-activity relationship; antitumor activity; 3-oxo-propionitrile; HCT116; T47D Cancer ranks second in diseases leading to mortality, following only cardiovascular diseases. One-quarter of all deaths in the United States are caused by cancer.1) Out of the many cancer diseases, breast cancer is the most prevalent cancer in women and represents the second highest leading cause of cancer death in this population after lung cancer.2) Colorectal cancer is the third most common cancer in both men and women, 91% of cases are diagnosed in individuals 50 years of age and older. 1) Chemotherapy is widely used to treat and control cell growth and limit the spread of cancer cells to other sites. Although, there is a success with certain forms of cancer, drug therapy has only limited impact against the three major killers: carcinoma of lung, breast and colorectal system. Therefore, there is a need to develop novel antitumor agents to treat and combat this disease.Several promising antitumor agents containing thiazolidine and thiazolidinone scaffolds have been identified to have a broad range of anticancer activities.3-14) Previously, we reported promising antitumor properties of a variety of 5-arylidene thiazolidinone derivatives Ia-c (Fig. 1) exhibiting considerable cytotoxic activity against colon HCT116 cancer cell lines compared with Doxorubicin (reference standard, IC 50 =0.00686 mM).15) In continuation of these previous findings and in order to optimize novel antitumor active agents possessing the same thiazolidinone core, it is intended in the present work to perform some modifications in the adopted structures via inserting heteroalicyclic amines (morpholinyl or piperidinyl functions, 4a-j) instead of the aromatic amines Ia-c due to their hydrophilic properties. Moreover, a series of heteroalicyclic methylene containing compounds 5a-h will be also prepared replacing the arylidene moiety of Ia-c (Fig. 1). Additionally, many morpholine and piperidine containing compounds were known as anticancer active agents that exerted their actions via inhibition of different targets such as phosphatidylinositol 3-kinases (PI3Ks) and histone deacetylase (HDAC). [16][17][18][19][20] Moreover, the piperidine deriva...

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Section: Resultsmentioning

confidence: 92%

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Hanna

George

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Thus, starting from a series of bifunctional sulfureoxygen or sulfurenitrogen pronucleophiles, or thioureas 119 in presence of tributylphosphine, a large number of 5-or 6-membered sulfur-containing rings 120 were prepared using an a-S-addition and subsequent intramolecular cyclization reaction (Scheme 54). 56 Using this approach, the authors synthesized several arylidene rhodanine derivatives, which possess multiple biological activities, in moderate to good yields, starting from dithiocarbamates as pronucleophiles. Later, the same authors reported that thioureas 121, bearing alkyl groups at nitrogen, reacted with ethyl phenylpropiolate (105) under tributylphosphine catalysis to give thiohydantoin derivatives 122/123 in moderate yields (Scheme 55).…”

Section: Nucleophilic Addition To the A-position Of Activated Alkynesmentioning

confidence: 99%

Organocatalytic transformations of alkynals, alkynones, propriolates, and related electron-deficient alkynes

et al. 2014

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“…For example, the reaction of dithiocarbamates (prepared in situ from amines and CS 2 ) and arylpropiolates in the presence of PBu 3 as a catalyst ( Table 9.4) led to alkylidine rhodanine-based scaffolds [20].…”

Section: Synthesis Of Rhodanine-based Scaffoldsmentioning

confidence: 99%

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

Rostamnia

Doustkhah

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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Rhodanine and thiazolidinone (TZD) heterocycles are attractive targets in organic and medicinal chemistry owing to their potency in a wide spectrum of biological activities and can also serve as synthetic intermediates for many kinds of pharmaceuticals or drug precursors. Consequently, looking for efficient and concise green methods for the synthesis of these types of compounds is a major challenge in chemistry. As a result, many green methods have been used to synthesize structurally complex and diverse rhodanine and TZDs in recent years. The purpose of this chapter is to discuss the recent green synthesis of the rhodanine and TZD heterocyclic scaffolds including aqueous medium synthesis, ionic liquid, microwave, ultrasonic irradiation, solvent-free methods, solid catalysts, such as mesoporous, magnetic nanoparticles, etc.

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Phosphine-Catalyzed Construction of Sulfur Heterocycles

Cited by 78 publications

References 18 publications

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Organocatalytic transformations of alkynals, alkynones, propriolates, and related electron-deficient alkynes

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

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