- Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex
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The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.
- Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
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supporting information
p. 1098 - 1102
(2019/05/16)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF DEXMETHYL PHENIDATE HYDROCHLORIDE
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Disclosed herein a process for the preparation of highly pure dexmethylphenidate hydrochloride (Formula-I) which comprises the steps of neutralization of dl- threomethylphenidate hydrochloride to dl-threo methylphenidate; subsequent resolution of dl-threo methylphenidate using amino acid or its derivatives as chiral resolution agent to yield dexmethylphenidate salt; hydrolysis of the salt and further conversion of dexmethylphenidate into its hydrochloride salt.
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Page/Page column 13
(2018/02/28)
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- "A NOVEL PROCESS FOR CHIRAL RESOLUTION OF HIGHLY PURE (6R)-6-(DIMETHYLAMINO)-4,4-DIPHENYL-3-HEPTANONE FROM RACEMIC METHADONE HYDROCHLORIDE"
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The present invention discloses an improved process for preparing pure (dimethylarnino)-4,4-diphenyl-3-heptanone and its hydrochloride salt.
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Page/Page column 10
(2016/07/27)
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- Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides
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Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).
- Paz, Nieves R.,Rodríguez-Sosa, Dionisio,Valdés, Haydee,Marticorena, Ricardo,Melián, Daniel,Copano, M. Belén,González, Concepción C.,Herrera, Antonio J.
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supporting information
p. 2370 - 2373
(2015/06/02)
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- N-Substituted Glutamyl Sulfonamides as Inhibitors of Glutamate Carboxypeptidase II (GCP2)
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Glutamate carboxypeptidase II (GCP2) is a membrane-bound cell-surface peptidase which is implicated in several neurological disorders and is also over-expressed in prostate tumor cells. There is a significant interest in the inhibition of GCP2 as a means of neuroprotection, while GCP2 inhibition as a method to treat prostate cancer remains a topic of further investigation. The key zinc-binding functional group of the well-characterized classes of GCP2 inhibitors (phosphonates and phosphoramidates) is tetrahedral and negatively charged at neutral pH, while glutamyl urea class of inhibitors possesses a planar and neutral zinc-binding group. This study introduces a new class of GCP2 inhibitors, N-substituted glutamyl sulfonamides, which possess a neutral tetrahedral zinc-binding motif. A library containing 15 secondary sulfonamides and 4 tertiary (N-methyl) sulfonamides was prepared and evaluated for inhibitory potency against purified GCP2 enzyme activity. While most inhibitors lacked potency at 100μm, short alkyl sulfonamides exhibited promising low micromolar potency, with the optimal inhibitor in this series being glutamyl N-(propylsulfonamide) (2g). Lastly, molecular docking was used to develop a model to formulate an explanation for the relative inhibitory potencies employed for this class of inhibitors. A small library of glutamyl sulfonamides was prepared and evaluated for in vitro potency against glutamate carboxypeptidase II (GCP2). Short alkyl sulfonamide inhibitors were the most potent, demonstrating low micromolar IC50 values.
- Blank, Brian R.,Alayoglu, Pinar,Engen, William,Choi, Joseph K.,Berkman, Clifford E.,Anderson, Marc O.
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p. 241 - 247
(2012/01/12)
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- SELECTIVE M4 RECEPTOR ANTAGONIST AND ITS MEDICAL USE
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The present invention provides a selective M4 receptor antagonist, levorotatory demethylated phencynonate or its nontoxic pharmaceutically acceptable salt, a pharmaceutical composition comprising this compound, and a use thereof in the manufacture of a medicament for the treatment of motion dysfunction, such as, tremor, rigor and the like caused by Parkinson's disease (PD). The structure, of the compound is shown in Formula IIa:
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Page/Page column 4
(2012/01/03)
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- SELECTIVE M4 RECEPTOR ANTAGONIST AND ITS MEDICAL USE
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The present invention provides a selective M4 receptor antagonist, levorotatory demethylated phencynonate or its nontoxic pharmaceutically acceptable salt, a pharmaceutical composition comprising this compound, and a use thereof in the manufacture of a medicament for the treatment of motion dysfunction, such as, tremor, rigor and the like caused by Parkinson's disease (PD). The structure of the compound is shown in Formula IIa:
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Page/Page column 5
(2009/12/23)
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- A new selective cleavage of N,N-dicarbamoyl-protected amines using lithium bromide
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A mild and new procedure for the selective cleavage of an alkoxycarbonyl group (Boc, CBz) in N,N-dicarbamoyl-protected amino compounds is described. The method is based on the use of lithium bromide in acetonitrile and is compatible with a large range of other functionalities present in the substrates. Compared with other reported methodologies, the procedure is particularly useful for the Cbz-selective cleavage in N,N-Ts,Cbz-diprotected amines. A rationalization of the selectivity supported by ab initio calculations is also presented.
- Hernandez, J. Nicolas,Ramirez, Miguel A.,Martin, Victor S.
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p. 743 - 746
(2007/10/03)
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- Syntheses, biological evaluation and QSAR study on antitumor activity of 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides
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We have reported [unpublished data] the synthesis and QSAR of 5-substituted-2-(substituted benzenesulphonyl) glutamines which have shown the importance of steric factor on the aliphatic chain. N-Phthalyl isoglutamine, having the substitution at position 1 of the glutamic acid moiety, is the metabolite of recently approved thalidomide for different types of tumors by US FDA. Based on these, 36 new 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides were synthesized, as tools for further elucidation of the structural requirements for antitumor activity. All the synthesized compounds were tested for antitumor activity against Ehrlich Ascites Carcinoma (EAC) in Swiss albino mice using tumor weight as inhibitory parameter. Quantitative structure-activity relationship (QSAR) studies of these analogues revealed that the electron donating groups on the phenyl ring are found to be mandatory for the activity which was also proved by the negative coefficient of indicator parameter I3, for NO2 group on the phenyl ring. Molecular volume (MV) and steric factor at R5 position also plays a role in ligand-receptor interactions.
- Srikanth,Debnath, Bikash,Jha, Tarun
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p. 1841 - 1854
(2007/10/03)
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- Synthesis, screening and quantitative structure-activity relationship (QSAR) studies of some glutamine analogues for possible anticancer activity
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We described the syntheses, biological activities and QSAR studies of 36 new 5-n-substituted-2-(substituted benzenesulphonyl) glutamines 6-41 with different substitutions. These compounds were designed as structural analogues of most reactive amino acid, 'glutamine' (GLN), especially in the tumor cells. They present the new basic lateral chains at R5 position as well as different substitutions at 2′, 3′, 4′, and 5′ positions on the benzene ring. The synthesized compounds have been tested for antitumor activity against Ehrlich ascites carcinoma (EAC) in Swiss albino mice using percentage inhibition of tumor weight as inhibitory parameter. In order to elucidate the structural requirements for antitumor activity, quantitative structure-activity relationship (QSAR) studies have been performed using extra thermodynamic model of Hansch. QSAR equations showed that the electronic parameter (σ) on the aromatic ring system, steric parameter (Es) and to some extent Sterimol length of the substituent (L) on the aliphatic side chain correlate significantly with the antitumor activity. Resonance factor occupies the major electronic contribution on the aromatic ring system to the activity.
- Srikanth,Kumar,Ghosh, Balaram,Jha, Tarun
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p. 2119 - 2131
(2007/10/03)
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- HIV protease inhibitors based on amino acid derivatives
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A compound selected from the group consisting of a compound of formula I 1a compound of formula II 2and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R1, R2, Cx, n, R3, R4, R5, Y are as defined in the specification.
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