3216-48-6Relevant academic research and scientific papers
Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source
Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng
, p. 7621 - 7627 (2017/07/26)
A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.
One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions
Ezawa, Masatoshi,Togo, Hideo
, p. 2379 - 2384 (2017/05/01)
A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.
D1-like receptors distinguishing thieno-azecine regioisomers
Abdel-Fattah, Mohamed A. O.,Abadi, Ashraf H.,Lehmann, Jochen,Schweikert, Peter M.,Enzensperger, Christoph
, p. 1679 - 1686 (2015/09/21)
Designing ligands with D1/D5 subtype selectivity is a challenge because of the high identity within the receptor helices. Based on the lead compounds 1-3, the thieno-benzazecine regioisomers 4 and 5 were synthesized and biologically evaluated for their affinity towards the five dopamine receptor subtypes utilizing a radioligand binding affinity technique. Within the D1-like family, compound 4 showed 20 fold selectivity for the D5 subtype over D1 subtype (Ki = 3 nM, D1: 60 nM), while its regioisomer, compound 5 with a reversed thiophene position, prefers the D1 subtype over the D5 subtype (Ki = 4 nM, D5: 15 nM). The benzothieno-benzazecine analog 6 was shown to be one of the few azecine derivatives with high affinity for both the D1- and the D2-like family members in the same order of magnitude (Ki = 1.5 nM for D2 and 1.9 nM for D5). Thorough analysis of the amino acid residues constituting the binding pockets of the target dopamine receptor subtypes revealed that at the D5 receptor, either serine S 6.62 and threonine T 7.33 residues or a water network, stabilized by anionic amino acids could contribute to the selectivity pattern of the synthesized compounds.
FUSED HETEROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF HISTONE DEACETYLASE
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Page/Page column 170-172, (2008/06/13)
Disclosed are compounds of formula (I) that inhibit histone deacetylase (HDAC) enzymatic activity, pharmaceutical compositions comprising such compounds, as well as methods to treat conditions, particularly proliferative conditions, mediated at least in part by HDAC, wherein A, W, W1, W2, Ar2, and G are described herein.
Modified ibogaine fragments: Synthesis and preliminary pharmacological characterization of 3-ethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5- b]benzothiophenes
Efange, Simon M. N.,Mash, Deborah C.,Khare, Anil B.,Ouyang, Quinjie
, p. 4486 - 4491 (2007/10/03)
Five phenyl-substituted derivatives and analogues of 1,2,3,4,5,6- hexahydroazepino[4,5-b]indole, 5, a major fragment of ibogaine (1), were synthesized and tested for binding to monoamine transporters, the NMDA receptor-coupled cation channel, and dopamine and opioid receptors. All five derivatives, 9 and 17a-d, displayed 8-10-fold higher affinity at the DA transporter than ibogaine and noribogaine (4). At the serotonin transporter, two compounds (9 and 17a) exhibited higher potency than ibogaine, while the rest had weaker binding affinities than the lead compound. In keeping with their structural similarity to ibogaine, all five compounds displayed weak to poor affinity for dopamine D1 and D2 receptors. However, two compounds, 17a,c, demonstrated moderate binding affinities at dopamine D3 receptors. All five compounds displayed weak to poor affinities for μ and κ opioid receptors and for the NMDA receptor-coupled cation channel. Despite the qualitative differences, derivatives and analogues of 5 may serve as useful substitutes for ibogaine.
Bioactive tricyclic ibogaine analogs
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, (2008/06/13)
Ibogaine analogs are provided, which are phenyl-substituted-hexahydroazepino[4,5-b]indoles useful to treat cocaine addiction and the use of other addictive substances.
Benzothiophen analogs as antiviral agents
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, (2008/06/13)
Benzothiophene analogs useful to treat herpes viral infections, particularly cytomegalovirus, are provided. These antiviral agents have the structural formula (I) STR1 wherein R and R1 are as defined herein, and may be in free base or acid addition salt form. Pharmaceutical compositions are provided containing the antiviral agents, as are methods of treating herpes-infected individuals.
Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides
Ellingboe,Alessi,Dolak,Nguyen,Tomer,Guzzo,Bagli,McCaleb
, p. 1176 - 1183 (2007/10/02)
A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).
