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[PMID]: 29408293
[Au] Autor:Bercu JP; Galloway SM; Parris P; Teasdale A; Masuda-Herrera M; Dobo K; Heard P; Kenyon M; Nicolette J; Vock E; Ku W; Harvey J; White A; Glowienke S; Martin EA; Custer L; Jolly RA; Thybaud V
[Ad] Address:Gilead Sciences, 333 Lakeside Drive, Foster City, CA, USA. Electronic address: jbercu@gilead.com.
[Ti] Title:Potential impurities in drug substances: Compound-specific toxicology limits for 20 synthetic reagents and by-products, and a class-specific toxicology limit for alkyl bromides.
[So] Source:Regul Toxicol Pharmacol;94:172-182, 2018 Feb 09.
[Is] ISSN:1096-0295
[Cp] Country of publication:Netherlands
[La] Language:eng
[Ab] Abstract:This paper provides compound-specific toxicology limits for 20 widely used synthetic reagents and common by-products that are potential impurities in drug substances. In addition, a 15 µg/day class-specific limit was developed for monofunctional alkyl bromides, aligning this with the class-specific limit previously defined for monofunctional alkyl chlorides. Both the compound- and class-specific toxicology limits assume a lifetime chronic exposure for the general population (including sensitive subpopulations) by all routes of exposure for pharmaceuticals. Inhalation-specific toxicology limits were also derived for acrolein, formaldehyde, and methyl bromide because of their localized toxicity via that route. Mode of action was an important consideration for a compound-specific toxicology limit. Acceptable intake (AI) calculations for certain mutagenic carcinogens assumed a linear dose-response for tumor induction, and permissible daily exposure (PDE) determination assumed a non-linear dose-response. Several compounds evaluated have been previously incorrectly assumed to be mutagenic, or to be mutagenic carcinogens, but the evidence reported here for such compounds indicates a lack of mutagenicity, and a non-mutagenic mode of action for tumor induction. For non-mutagens with insufficient data to develop a toxicology limit, the ICH Q3A qualification thresholds are recommended. The compound- and class-specific toxicology limits described here may be adjusted for an individual drug substance based on treatment duration, dosing schedule, severity of the disease and therapeutic indication.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1802
[Cu] Class update date: 180307
[Lr] Last revision date:180307
[St] Status:Publisher

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[PMID]: 29512313
[Au] Autor:Yu H; Koocher N; Rondinelli J; Halasyamani PS
[Ad] Address:UNITED STATES.
[Ti] Title:Pb2BO3I: A New Borate Iodide with the Largest SHG Response in the KBe2BO3F2 (KBBF) Family.
[So] Source:Angew Chem Int Ed Engl;, 2018 Mar 07.
[Is] ISSN:1521-3773
[Cp] Country of publication:Germany
[La] Language:eng
[Ab] Abstract:Borate halides are an ideal materials class from which to design high-performance nonlinear optical (NLO) materials. Currently, borate fluorides, chlorides, and bromides are extensively investigated while borate iodide materials discovery remains rare due to perceived synthetic challenges. We report a new borate iodide, Pb2BO3I synthesized by a straightforward hydrothermal method. The Pb2BO3I chemical formula conceals that the compound exhibits a structure similiar to the well-known KBe2BO3F2 (KBBF), which we show supports the highest second-harmonic generation (SHG) at 1064 nm in the KBBF family, 10 x KH2PO4 (KDP), arising from the inclusion of Pb2+ and I- and the aforementioned crystal-chemistry. Our work shows that KBBF-related compounds can be synthesized in iodide chemistries to exhibit superior NLO reponses.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1803
[Cu] Class update date: 180307
[Lr] Last revision date:180307
[St] Status:Publisher
[do] DOI:10.1002/anie.201802079

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[PMID]: 29512252
[Au] Autor:Moon PJ; Fahandej-Sadi A; Qian W; Lundgren RJ
[Ad] Address:CANADA.
[Ti] Title:Decarboxylative Benzylation of sp2-Organoboron Reagents.
[So] Source:Angew Chem Int Ed Engl;, 2018 Mar 07.
[Is] ISSN:1521-3773
[Cp] Country of publication:Germany
[La] Language:eng
[Ab] Abstract:The Cu-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation protocols (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated via aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1803
[Cu] Class update date: 180307
[Lr] Last revision date:180307
[St] Status:Publisher
[do] DOI:10.1002/anie.201800829

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[PMID]: 29503480
[Au] Autor:Ansari NH; Söderberg BCG
[Ad] Address:C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States.
[Ti] Title:Synthesis of -alkoxy-substituted 2 -benzimidazoles.
[So] Source:Tetrahedron Lett;58(50):4717-4720, 2017 Dec 13.
[Is] ISSN:0040-4039
[Cp] Country of publication:England
[La] Language:eng
[Ab] Abstract:Treatment of 2-nitro- -(2-methyl-1-propen-1-yl)benzenamines with potassium -butoxide in -butanol followed by the addition of an electrophile affords -alkoxy-2 -benzimidazoles. Electrophiles including methyl iodide, allylic bromides, propargylic bromides, benzyl bromide, and acetyl chloride gave good to excellent yields of product while 1-iodo- and 2-iodo-butane afforded very low yields.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1803
[Cu] Class update date: 180307
[Lr] Last revision date:180307
[St] Status:In-Data-Review
[do] DOI:10.1016/j.tetlet.2017.11.007

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[PMID]: 29430922
[Au] Autor:Cavallaro G; Lazzara G; Milioto S; Parisi F; Evtugyn V; Rozhina E; Fakhrullin R
[Ad] Address:Dipartimento di Fisica e Chimica , Università degli Studi di Palermo , Viale delle Scienze, pad. 17, 90128 Palermo , Italy.
[Ti] Title:Nanohydrogel Formation within the Halloysite Lumen for Triggered and Sustained Release.
[So] Source:ACS Appl Mater Interfaces;10(9):8265-8273, 2018 Mar 07.
[Is] ISSN:1944-8252
[Cp] Country of publication:United States
[La] Language:eng
[Ab] Abstract:An easy strategy to obtain nanohydrogels within the halloysite nanotube (HNTs) lumen was investigated. Inorganic reverse micelles based on HNTs and hexadecyltrimethylammonium bromides were dispersed in chloroform, and the hydrophilic cavity was used as a nanoreactor to confine the gel formation based on alginate cross-linked by calcium ions. Spectroscopy and electron microscopy experiments proved the confinement of the polymer into the HNT lumen and the formation of calcium-mediated networks. Biological tests proved the biocompatibility of the hybrid hydrogel. The nanogel in HNTs was suitable for drug loading and sustained release with the opportunity of triggered burst release by chemical stimuli. Here, we propose a new strategy based on inorganic reverse micelles for nanohydrogel formation, which are suitable for industrial and biological applications as well as for selective and triggered adsorption and/or release.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1802
[Cu] Class update date: 180307
[Lr] Last revision date:180307
[St] Status:In-Data-Review
[do] DOI:10.1021/acsami.7b19361

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[PMID]: 29505625
[Au] Autor:Bijoy TK; Murugan P; Kumar V
[Ad] Address:Dr Vijay Kumar Foundation, 1969 Sector 4, Gurgaon 122001, Haryana, India. kumar@vkf.in vijay.kumar@snu.edu.in and Academy of Scientific and Innovative Research (AcSIR)-CSIR-Central Electrochemical Research Institute, Karaikudi 630003, Tamil Nadu, India.
[Ti] Title:Atomic structure and electronic properties of A B XY (A = Si-Pb, B = Cl-I, and XY = PN and SiS) inorganic double helices: first principles calculations.
[So] Source:Phys Chem Chem Phys;, 2018 Mar 05.
[Is] ISSN:1463-9084
[Cp] Country of publication:England
[La] Language:eng
[Ab] Abstract:We study the structural stability and electronic properties of new classes of DNA-like inorganic double helices of the type A B XY (A = Si-Pb, B = Cl-I, and XY = PN and SiS) by employing first principles density functional theory (DFT) calculations including van der Waals interactions. In these quaternary double helices PN or SiS forms the inner helix while the AB helix wraps around the inner helix and the two are interconnected. We find that the bromides and iodides of Ge, Sn, and Pb as well as Pb Cl PN form structurally stable double helices while Ge I SiS as well as bromides and iodides of Sn and Pb have stable double helices. The atomic structures of different double helices have been analyzed in detail to understand the stability of these systems as there is up to about 80% difference in the interatomic distances in the two helices which is remarkable. Also in these new classes of double helices there is polar covalent bonding in the inner helix due to heteroatoms. We have calculated the DDEC6 partial atomic charges and bond orders which suggest strong covalent bonding in the inner helix. The electronic structure reveals that these double helices are semiconducting and in many cases the band gap is direct. Furthermore, we have studied the effects of doping and found that hole doping is the most appropriate way to tuning their electronic properties.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1803
[Cu] Class update date: 180305
[Lr] Last revision date:180305
[St] Status:Publisher
[do] DOI:10.1039/c7cp08231b

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[PMID]: 29499901
[Au] Autor:Kaszás T; Ivanov A; Tóth M; Ehlers P; Langer P; Somsák L
[Ad] Address:Department of Organic Chemistry, University of Debrecen, POB 400, H-4002 Debrecen, Hungary; Department of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
[Ti] Title:Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals.
[So] Source:Carbohydr Res;, 2018 Feb 19.
[Is] ISSN:1873-426X
[Cp] Country of publication:Netherlands
[La] Language:eng
[Ab] Abstract:Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiOtBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1803
[Cu] Class update date: 180303
[Lr] Last revision date:180303
[St] Status:Publisher

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[PMID]: 29436837
[Au] Autor:Jin W; Zhou Y; Zhao Y; Ma Q; Kong L; Zhu G
[Ad] Address:Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
[Ti] Title:Nickel-Catalyzed Remote Arylation of Alkenyl Aldehydes Initiated by Radical Alkylation with Tertiary α-Carbonyl Alkyl Bromides.
[So] Source:Org Lett;20(5):1435-1438, 2018 Mar 02.
[Is] ISSN:1523-7052
[Cp] Country of publication:United States
[La] Language:eng
[Ab] Abstract:A novel nickel-catalyzed remote arylation of alkenyl aldehydes triggered by radical alkylation with tertiary α-carbonyl alkyl bromides is described, thus producing a quaternary carbon center containing ketones in promising yields with broad functional group compatibility. Preliminary mechanistic studies suggest that the combination of a 1,n-HAT (n = 5 or 6) from alkyl radicals to aldehyde C-H bonds with nickel catalysis may account for the realization of this reaction.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1802
[Cu] Class update date: 180302
[Lr] Last revision date:180302
[St] Status:In-Data-Review
[do] DOI:10.1021/acs.orglett.8b00221

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[PMID]: 29406714
[Au] Autor:Kumar SV; Ma D
[Ad] Address:State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
[Ti] Title:Synthesis of N-(Hetero)aryl Carbamates via CuI/MNAO Catalyzed Cross-Coupling of (Hetero)aryl Halides with Potassium Cyanate in Alcohols.
[So] Source:J Org Chem;83(5):2706-2713, 2018 Mar 02.
[Is] ISSN:1520-6904
[Cp] Country of publication:United States
[La] Language:eng
[Ab] Abstract:An efficient route to N-(hetero)aryl carbamates was developed through CuI/MNAO [2-((2-methylnaphthalen-1-yl)amino)-2-oxoacetic acid] catalyzed cross-coupling of (hetero)aryl chlorides with potassium cyanate in alcohols at 120-130 °C. This method utilizes broadly available substrates to afford various N-(hetero)aryl carbamates in good to excellent yields. Moreover, (hetero)aryl bromides and (hetero)aryl iodides were also reacted at low catalyst loadings and relatively low temperatures to provide N-(hetero)aryl carbamates.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1802
[Cu] Class update date: 180302
[Lr] Last revision date:180302
[St] Status:In-Data-Review
[do] DOI:10.1021/acs.joc.7b03175

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[PMID]: 29241011
[Au] Autor:Coomber CE; Benhamou L; Bucar DK; Smith PD; Porter MJ; Sheppard TD
[Ad] Address:Department of Chemistry, Christopher Ingold Laboratories, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
[Ti] Title:Silver-Free Palladium-Catalyzed C(sp )-H Arylation of Saturated Bicyclic Amine Scaffolds.
[So] Source:J Org Chem;83(5):2495-2503, 2018 Mar 02.
[Is] ISSN:1520-6904
[Cp] Country of publication:United States
[La] Language:eng
[Ab] Abstract:Herein, we report a silver-free Pd(II)-catalyzed C(sp )-H arylation of saturated bicyclic and tricyclic amine scaffolds. The reaction provides good yields using a range of aryl iodides and aryl bromides including functionalized examples bearing aldehydes, ketones, esters, free phenols, and heterocycles. The methodology has been applied to medicinally relevant scaffolds. Two of the intermediate palladium complexes in the catalytic cycle have been prepared and characterized, and a mechanism is proposed. Removal of the directing group proceeded with good yield under relatively mild conditions.
[Pt] Publication type:JOURNAL ARTICLE
[Em] Entry month:1712
[Cu] Class update date: 180302
[Lr] Last revision date:180302
[St] Status:In-Data-Review
[do] DOI:10.1021/acs.joc.7b02665


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