56473-97-3Relevant academic research and scientific papers
3-Nitrene-2-formylthiophene and 3-Nitrene-2-formylfuran: Matrix Isolation, Conformation, and Rearrangement Reactions
Liu, Jie,Qian, Weiyu,Wang, Lina,Wu, Zhuang,Yang, Yang,Zeng, Xiaoqing
, p. 3786 - 3794 (2020)
Two new heteroarylnitrenes, 3-nitrene-2-formylthiophene (15/15′) and 3-nitrene-2-formylfuran (16/16′), in the triplet ground state have been generated in solid Ar (10.0 K) and N2 (15.0 K) matrices by the 266 nm laser photolysis of 3-azido-2-formylthiophene (13) and 3-azido-2-formylfuran (14), respectively. According to the characterization with matrix-isolation IR spectroscopy and quantum chemical calculations at the B3LYP/6-311++G(3df,3pd) level, both nitrenes exhibit two conformations depending on the orientation of the formyl groups. Upon subsequent green-light irradiation (532 nm), both the nitrenes 15/15′ and 16/16′ undergo ring closure to form 3,2-thienoisoxazole (17) and 3,2-furoisoxazole (18), respectively. Traces of 3-imino-4,5-dihydrothiophene-2-ketene (19), formally formed through the intramolecular 1,4-H shift in the corresponding nitrenes 15/15′, have been also identified among the laser photolysis products of the azide 13. In sharp contrast to the photochemistry, the high-vacuum flash pyrolysis (HVFP) of the azide 13 at ca. 1000 K mainly yields imino ketene in two conformations 19/19′ together with traces of isoxazole 17. In addition to the reversible conformational interconversion in the imino ketene 19 ? 19′, the photoisomerization from isoxazole 17 to imino ketene 19 has also been observed. The HVFP of the azide 14 at ca. 1000 K results in complete dissociation to HCN, C2H2, CO, CO2, H2O, and N2. Unlike the recently disclosed hydrogen-atom tunneling (HAT) in the transformation from the structurally related 2-formyl phenylnitrene (2) to imino ketene 3 in a cryogenic Ar-matrix, the absence of HAT in nitrenes 15 and 16 can be reasonably explained by the higher barrier heights and also larger barrier widths in the isomerization reactions.
INDAZOLES AND AZAINDAZOLES AS LRRK2 INHIBITORS
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Page/Page column 197; 198, (2021/01/29)
The present invention is directed to indazole and azaindazole compounds which are inhibitors of LRRK2 and are useful in the treatment of CNS disorders.
FUSED DIHYDRO-4H-PYRAZOLO[5,1-C][1,4]OXAZINYL COMPOUNDS AND ANALOGS FOR TREATING CNS DISORDERS
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Paragraph 0203, (2016/09/22)
Disclosed are compounds of Formula (I) and pharmaceutically acceptable salts thereof, wherein Ring B, A1, A2, R6, w and n1 are defined and described herein; compositions thereof; and methods of use thereof. These compounds are useful for treating a variety of neurological and psychiatric disorders, such as those described herein.
ARYL RECEPTOR MODULATORS AND METHODS OF MAKING AND USING THE SAME
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Paragraph 00173-00175, (2016/04/26)
The present invention is generally directed towards compounds capable of binding the aryl hydrocarbon receptor and modulating its activity,methods of treating inflammatory conditions such as Crohn's disease using such compounds, and pharmaceutical compositions comprising such compounds. Also provided are methods of increasing levels of IL-22 in a subject and/or decreasing levels of IFN-γ in a subject.
TRIAZOLOTHIENOPYRIMIDINE COMPOUND INHIBITORS OF UREA TRANSPORTERS AND METHODS OF USING INHIBITORS
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Page/Page column 68, (2013/10/21)
Provided herein are small molecule triazolothienopyrimidine compounds that inhibit urea transport activity of solute transporters, particularly the UT-B transporter. The compounds described herein are useful for increasing solute clearance in states of fluid overload and for treating refractory edema associated with cardiovascular, renal, and metabolic diseases, disorders, and conditions.
Nanomolar potency and metabolically stable inhibitors of kidney urea transporter UT-B
Anderson, Marc O.,Zhang, Jicheng,Liu, Yan,Yao, Chenjuan,Phuan, Puay-Wah,Verkman
scheme or table, p. 5942 - 5950 (2012/07/30)
Urea transporters, which include UT-B in kidney microvessels, are potential targets for development of drugs with a novel diuretic ('urearetic') mechanism. We recently identified, by high-throughput screening, a triazolothienopyrimidine UT-B inhibitor, 1, that selectively and reversibly inhibited urea transport with IC50 = 25.1 nM and reduced urinary concentration in mice (Yao et al.J. Am. Soc. Nephrol., in press). Here, we analyzed 273 commercially available analogues of 1 to establish a structure-activity series and synthesized a targeted library of 11 analogues to identify potent, metabolically stable UT-B inhibitors. The best compound, {3-[4-(1,1-difluoroethyl)benzenesulfonyl]thieno[2,3-e][1,2,3]triazolo[1,5-a] pyrimidin-5-yl}thiophen-2-ylmethylamine, 3k, had IC50 of 23 and 15 nM for inhibition of urea transport by mouse and human UT-B, respectively, and ～40-fold improved in vitro metabolic stability compared to 1. In mice, 3k accumulated in kidney and urine and reduced maximum urinary concentration. Triazolothienopyrimidines may be useful for therapy of diuretic-refractory edema in heart and liver failure.
Synthesis of 9-amino-5,6,7,8-tetrahydrothieno[3,2-b]quinoline and 9-amino-5,6,7,8-tetrahydrothieno[3,2-b]quinolin-8-ol derivatives
Song, Yang-Heon,Jo, Boung Sun
experimental part, p. 1132 - 1136 (2010/03/03)
(Chemical Equation Presented) The synthesis of 9-amino-5,6,7,8- tetrahydrothieno[3,2-b]quinoline (3) and 9-amino-5,6,7,8-tetrahydrothieno[ 3,2-b]quinolin-5-ol derivatives (4a-g) in good yield by three-step procedures starting from 3-aminothiophene-2-carbonitrile and 5-substituted cyclohexane-1,3-dione is described.
Synthesis of thienoimidazo[4,5-b]pyridines and thenylidenoimidazolinones
Bjoerk, Malin,Grivas, Spiros
, p. 2369 - 2380 (2007/10/03)
The two isomers 2-amino-1-methylimidazo[4,5-b]thieno[3,2-e]pyridine (3) and 2-amino-1-methylimidazo[4,5-b]thieno[2,3-e]pyridine (4) were synthesized by the Friedlaender reaction starting from creatinine and the appropriate aminothiophenecarbaldehydes (11 and 13). Creatinine was also condensed with 2-nitro-3-thiophenecarbaldehyde (10) in ethylene glycol to yield the 2-amino-1-methyl-5-[2-(2-nitro-3-thenylidene)]-2-imidazolin-4-one (7a), with 3-amino-2-thiophenecarbaldehyde (13) under Perkin conditions to yield 2-acetamido-5-[2-(3-acetamido-2-thenylidene)]-1-methyl-2-imidazolin-4-on e (8), and with 4-azido-3-thiophenecarbaldehyde (17) in acetic acid to yield 2-amino-5-[2-(4-azido-3-thenylidene)]-1-methyl-2-imidazolin-4-one (9). The thenylidenoimidazolinone (8) was converted into compound (4).{A figure is presented}.
Ring Cleavage of a 3-Azidothiophene: Novel Extrusion of Acetylene
Moody, Christopher J.,Rees, Charles W.,Tsoi, Siu Chung
, p. 915 - 920 (2007/10/02)
Mild thermal decomposition of ethyl 2-azido-3-(3-azido-2-thienyl)propenoate (8) results in the cleavage of the thiophene ring with extrusion of acetylene and formation of ethyl 5-cyanoisothiazole-3-carboxylate (10), together with ethyl thienopyridazine-3-carboxylate (9).The former reaction represents the first fragmentation of a five-membered heteroaromatic β-nitrene to extrude an acetylene, and the latter reaction is a rare example of formal intramolecular coupling of nitrenes in solution themolysis.This vinyl azide group is necessary for this cleavage of the thiophene ring and a mechanism is proposed in which the derived nitrene co-ordinates with the thiophene sulphur atom to facilitate ring fragmentation.The analogous furan does not fragment similarly.Diels-Alder cycloadditions of 4-phenyl-1,2,4-triazole-3,5-dione to 2-vinylthiophenes were investigated as an independent approach to the thienopyridazine system, but the fused 4-phenyl-1,2,4-triazoline-3,5-dione ring proved resistant to hydrolytic cleavage.
