N-Alkylation of imides using phase transfer catalysts under solvent-free conditions
TL;DR: In this paper, a solvent-free N-Alkylation of imides and alkylhalides under PT catalysts under solvent free conditions has been developed, where the reaction occurs in the presence of K2CO3 and in many cases it takes place spontaneously.
About: This article is published in Journal of Heterocyclic Chemistry.The article was published on 2008-09-01. It has received 26 citations till now. The article focuses on the topics: Alkylation & Catalysis.
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TL;DR: A general, efficient strategy for large-area 2DMCs that grows crystals on water surface to minimize the density of nuclei by controlling the interfacial tension of the water/solution system with a phase transfer surfactant.
Abstract: Two-dimensional molecular crystals (2DMCs) are a promising candidate for flexible and large-area electronics. Their large-area production requires both low nuclei density and 2D crystal growth mode. As an emerging type of material, their large-area production remains a case-by-case practice. Here we present a general, efficient strategy for large-area 2DMCs. The method grows crystals on water surface to minimize the density of nuclei. By controlling the interfacial tension of the water/solution system with a phase transfer surfactant, the spreading area of the solvent increases tens of times, leading to the space-confined 2D growth of molecular crystals. As-grown sub-centimeter-sized 2DMCs floating on the water surface can be easily transferred to arbitrary substrates for device applications.
124 citations
Patent•
09 May 2013TL;DR: In this article, the authors present methods of synthesizing heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods for their use for the treatment, prevention, and management of various disorders such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.
Abstract: Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.
70 citations
TL;DR: The new azo compounds I(a-c) and II(a) were prepared by the reaction of I and II with three different aromatic amines, namely aniline, p-aminophenol and p-toluidine.
Abstract: Maleic anhydride was reacted with p -aminophenol and p -toluidine in the presence of di-phosphorus pentoxide (P 2 O 5 ) as a catalyst to produce two compounds: N -(4-hydroxy-phenyl)maleimide ( I ) and N -(4-methylphenyl)maleimide ( II ). The new azo compounds I(a-c) and II(a-c) were prepared by the reaction of I and II with three different aromatic amines, namely aniline, p -aminophenol and p -toluidine. The structures of these compounds were confirmed by CHN, FT-IR, 1 H-NMR, 13 C-NMR, mass spectrum and UV/Vis spectroscopy. Keywords: synthesis; azo compounds; aromatic amines; N-(4-hydroxylpheneyl)maleimide 1. Introduction Small molecules and macromolecules containing imide groups exhibit great electrical properties, good solubility in polar media, resistance to hydrolysis and high thermal stability [1-8]. Due to their excellent properties many efforts have been made to produce different compounds containing imide groups consisting of two carbonyl groups bound to nitrogen. The most common unsubstituted cyclic imides were prepared by heating dicarboxylic acids or their anhydrides with reactants including ammonia, urea, formamide lithium nitride or primary amines [9-12], but the reaction needs to be carried out at high temperatures for efficient ring closure. Recently, attempts at preparing imide compounds either by the
58 citations
Cites methods from "N-Alkylation of imides using phase ..."
...conventional technique or via the microwave irradiation using various catalysts such as Lewis acids, hexamethyldisilazane, carbonyldiimidazole, 4-N,N-dimethylaminopyridine, ammonium chloride, hydroxylamine hydrochloride and sodium acetate to minimize the temperature and time of the reaction have been published [13-18]....
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TL;DR: This protocol describes the synthesis of two classes of clathrin inhibitors, Pitstop 1 and Pitstop 2, along with two inactive analogs that can be used as negative controls (Pitstop inactive controls, Pit not-2 and Pitnot-2-100), enabling cost-effective in-house synthesis for users of these inhibitor classes.
Abstract: This protocol describes the synthesis of two classes of clathrin inhibitors, Pitstop 1 and Pitstop 2, along with two inactive analogs that can be used as negative controls (Pitstop inactive controls, Pitnot-2 and Pitnot-2-100). Pitstop-induced inhibition of clathrin TD function acutely interferes with clathrin-mediated endocytosis (CME), synaptic vesicle recycling and cellular entry of HIV, whereas clathrin-independent internalization pathways and secretory traffic proceed unperturbed; these reagents can, therefore, be used to investigate clathrin function, and they have potential pharmacological applications. Pitstop 1 is synthesized in two steps: sulfonation of 1,8-naphthalic anhydride and subsequent reaction with 4-amino(methyl)aniline. Pitnot-1 results from the reaction of 4-amino(methyl)aniline with commercially available 4-sulfo-1,8-naphthalic anhydride potassium salt. Reaction of 1-naphthalene sulfonyl chloride with pseudothiohydantoin followed by condensation with 4-bromobenzaldehyde yields Pitstop 2. The synthesis of the inactive control commences with the condensation of 4-bromobenzaldehyde with the rhodanine core. Thioketone methylation and displacement with 1-napthylamine affords the target compound. Although Pitstop 1-series compounds are not cell permeable, they can be used in biochemical assays or be introduced into cells via microinjection. The Pitstop 2-series compounds are cell permeable. The synthesis of these compounds does not require specialist equipment and can be completed in 3-4 d. Microwave irradiation can be used to reduce the synthesis time. The synthesis of the Pitstop 2 family is easily adaptable to enable the synthesis of related compounds such as Pitstop 2-100 and Pitnot-2-100. The procedures are also simple, efficient and amenable to scale-up, enabling cost-effective in-house synthesis for users of these inhibitor classes.
36 citations
01 Jan 2014
TL;DR: In this article, the authors describe the synthesis of two classes of clathrin inhibitors, Pitstop 1 and Pitstop 2, along with two inactive analogs that can be used as negative controls (Pitstop inactive controls, Pitnot-2 and Pitnot 2-100).
Abstract: This protocol describes the synthesis of two classes of clathrin inhibitors, Pitstop 1 and Pitstop 2, along with two inactive analogs that can be used as negative controls (Pitstop inactive controls, Pitnot-2 and Pitnot-2-100). Pitstop-induced inhibition of clathrin TD function acutely interferes with clathrin-mediated endocytosis (CME), synaptic vesicle recycling and cellular entry of HIV, whereas clathrin-independent internalization pathways and secretory traffic proceed unperturbed; these reagents can, therefore, be used to investigate clathrin function, and they have potential pharmacological applications. Pitstop 1 is synthesized in two steps: sulfonation of 1,8-naphthalic anhydride and subsequent reaction with 4-amino(methyl)aniline. Pitnot-1 results from the reaction of 4-amino(methyl)aniline with commercially available 4-sulfo-1,8-naphthalic anhydride potassium salt. Reaction of 1-naphthalene sulfonyl chloride with pseudothiohydantoin followed by condensation with 4-bromobenzaldehyde yields Pitstop 2. The synthesis of the inactive control commences with the condensation of 4-bromobenzaldehyde with the rhodanine core. Thioketone methylation and displacement with 1-napthylamine affords the target compound. Although Pitstop 1–series compounds are not cell permeable, they can be used in biochemical assays or be introduced into cells via microinjection. The Pitstop 2–series compounds are cell permeable. The synthesis of these compounds does not require specialist equipment and can be completed in 3–4 d. Microwave irradiation can be used to reduce the synthesis time. The synthesis of the Pitstop 2 family is easily adaptable to enable the synthesis of related compounds such as Pitstop 2-100 and Pitnot-2-100. The procedures are also simple, efficient and amenable to scale-up, enabling cost-effective in-house synthesis for users of these inhibitor classes.
27 citations
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191 citations
TL;DR: In these series, compound 3e (LASSBio 468), having a sulfonyl-thiomorpholine moiety, showed potent inhibitory activity on LPS-induced neutrophil recruitment with ED(50)=2.5mg kg(-1), which was correlated with its inhibitory effect on TNF-alpha level.
183 citations
TL;DR: The effects of bridge length and conformation on the biological activity of these potential antipsychotic agents are discussed and two types of folded structures and several conformationally restrained analogues were synthesized.
Abstract: A series of phthalimide and isoindolinone derivatives bridged to 4-(1,2-benzisothiazol-3-yl)-1-piperazinyl was prepared The compounds were evaluated in vitro at dopamine D2 and serotonin 5-HT1a and 5-HT2 receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice The effects of bridge length and conformation on the biological activity of these potential antipsychotic agents are discussed A four-carbon spacer provided optimal activity within the two homologous series Conformational investigations of the lead compound, isoindolinone 2, were conducted in an attempt to account for the superior activity observed for the butyl derivatives On the basis of NMR and molecular modeling studies, two types of folded structures were proposed and several conformationally restrained analogues were synthesized In general, restrictions incorporated within the linking bridge were detrimental to activity
177 citations
TL;DR: The development of arylpiperazine derivatives acting at 5-HT(1A)Rs with an emphasis on structure-affinity relationships of agonists and antagonists, ligand-receptor interactions and pharmacological applications is reviewed.
Abstract: Serotonin (5-hydroxytryptamine, 5-HT) is one of the most attractive targets for medicinal chemists. Among 5-HTRs, the 5-HT(1A) subtype is the best studied and it is generally accepted that it is involved in psychiatric disorders such as anxiety and depression. Several structurally different compounds are known to bind 5-HT(1A)R sites. Among these, arylpiperazine derivatives represent one of the most important classes of 5-HT(1A)R ligands. This article will review the development of arylpiperazine derivatives acting at 5-HT(1A)Rs with an emphasis on structure-affinity relationships of agonists and antagonists, ligand-receptor interactions and pharmacological applications.
148 citations
TL;DR: For the 72 compounds presented here, an extended and more linear conformation in the aliphatic or aryl spacers turned out to be crucial for dopamine D3 receptor selectivity.
Abstract: The dopamine D3 receptor is recognized as a potential therapeutic target for the treatment of various neurological and psychiatric disorders Targetting high affinity and D3 versus D2 receptor-preferring ligands, the partial agonist BP 897 was taken as a lead structure Variations in the spacer and the aryl moiety led to N-alkylated 1-(2-methyoxyphenyl)piperazines with markedly improved affinity and selectivity Molecular modeling studies supported the structural development Pharmacophore models for dopamine D2 and D3 receptor ligands were developed from their potentially bioactive conformation and were compared in order to get insight into molecular properties of importance for D2/D3 receptor selectivity For the 72 compounds presented here, an extended and more linear conformation in the aliphatic or aryl spacers turned out to be crucial for dopamine D3 receptor selectivity Structural diversity in the aryl moiety (benzamides, heteroarylamides, arylimides) had a major influence on (sub)nanomolar D3 rec
114 citations