138408-36-3Relevant academic research and scientific papers
ISOQUINOLINES AS INHIBITORS OF HPK1
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Paragraph 2233; 2234, (2018/10/21)
Isoquinoline compounds and their use as inhibitors of HPK1 (hematopoietic kinase 1) are described. The compounds are useful in treating HPK1-dependent disorders and enhancing an immune response. Also described are methods of inhibitng HPK1, methods of treating HPK1-dependent disorders, methods for enhancing an immune response, and methods for preparing the isoquinoline compounds.
Thermal 1,3-Trityl migrations in diels-alder domino reactions of 1-Trityl-4-vinyl-1 H-imidazoles
Cotterill, Lynsey J.,Harrington, Ross W.,Clegg, William,Hall, Michael J.
supporting information; experimental part, p. 4604 - 4607 (2010/10/02)
(Figure presented) Under thermal conditions, tritylimidazoles have been shown to undergo sterically driven N→N trityl migrations, in disagreement with previously published reports. These migrations are a key step in several highly diastereoselective domin
Synthesis of 7-15N-oroidin and evaluation of utility for biosynthetic studies of pyrrole-imidazole alkaloids by microscale 1H-15N HSQC and FTMS
Wang, Yong-Gang,Morinaka, Brandon I.,Reyes, Jeremy Chris P.,Wolff, Jeremy J.,Romo, Daniel,Molinski, Tadeusz F.
supporting information; experimental part, p. 428 - 434 (2010/08/06)
Numerous marine-derived pyrrole-imidazole alkaloids (PIAs), ostensibly derived from the simple precursor oroidin, 1a, have been reported and have garnered intense synthetic interest due to their complex structures and in some cases biological activity; however very little is known regarding their biosynthesis. We describe a concise synthesis of 7-15N-oroidin (Id) from urocanic acid and a direct method for measurement, of 15N incorporation by pulse labeling and analysis by 1D 1H-15N HSQC NMR and FTMS. Using a mock pulse labeling experiment, we estimate the limit of detection (LOD) for incorporation of newly biosynthesized PIA by 1D 1H-15N HSQC to be 0.96 μg equivalent of 15N-oroidin (2.4 nmole) in a background of 1500 μg of unlabeled oroidin. (about 1 part per 1600). 7-15N-Oroidin will find utility in biosynthetic feeding experiments with live sponges to provide direct information to clarify the pathways leading to more complex pyrrole-imidazole alkaloids.
New high affinity H3 receptor agonists without a basic side chain
Kitbunnadaj, Ruengwit,Hoffmann, Marcel,Fratantoni, Silvina A.,Bongers, Gerold,Bakker, Remko A.,Wieland, Kerstin,El Jilali, Ahmed,De Esch, Iwan J. P.,Menge, Wiro M. P. B.,Timmerman, Henk,Leurs, Rob
, p. 6309 - 6323 (2007/10/03)
In this study, we replaced the basic amine function of the known histamine H3 receptor agonists imbutamine or immepip with non-basic alcohol or hydrocarbon moieties. All compounds in this study show a moderate to high affinity for the cloned human H3 receptor and, unexpectedly, almost all of them act as potent agonists. Moreover, in the alcohol series, we consistently observed an increased selectivity for the human H3 receptor over the human H4 receptor, but none of the compounds in this series possess increased affinity and functional activity compared to their alkylamine congeners. In this new series of compounds VUF5657, 5-(1H-imidazol-4-yl)-pentan-1-ol, is the most potent histamine H3 receptor agonist (pKi = 8.0 and pEC50 = 8.1) with a 320-fold selectivity at the human H3 receptor over the human H 4 receptor.
New building blocks for fluorinated bioimidazole derivatives II: Preparation of β-fluorourocanic acids
Dolensky, Bohumil,Kirk, Kenneth L.
, p. 3468 - 3473 (2007/10/03)
Replacement of vinyl hydrogen with fluorine is based on addition of an FBr equivalent to a double bond followed by HBr elimination. This sequence has been adapted to prepare 3-fluoro-3-imidazolylpropenoic acids (β-fluorourocanic acids), and the related fl
PYRAZINONE, PYRIDINONE, PIPERIDINE AND PYRROLIDINE THROMBIN INHIBITORS
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, (2008/06/13)
A compound which inhibits human thrombin and where has the structure and pharmaceutically acceptable salts thereof, wherein such as STR1 which are useful for inhibiting formation of blood platelet aggregates in blood in a mammal.
A new type of carboxypeptidase A inhibitors designed using an imidazole as a zinc coordinating ligand
Lee, Kyung Joo,Joo, Keum Chan,Kim, Eun-Jung,Lee, Mijoon,Kim, Dong H.
, p. 1989 - 1998 (2007/10/03)
2-(4-Imidazoyl)hydrocinnamic acid (1) and its congeners (2-4) having different length of alkyl chain spacers between the imidazole ring and the α-carbon to the carboxylate of 1 have been designed, synthesized and evaluated as inhibitors for carboxypeptidase A to show that they are competitive inhibitors for the enzyme. Inhibitor 1 was most potent having the K(i) value of 0.8 μM. The present study demonstrates that imidazole ring is an effective zinc coordinating ligand that can be useful for the design of inhibitors for zinc proteases.
Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and some 3-(1H-imidazol-4-yl)propanamines
Sellier, Christian,Buschauer, Armin,Elz, Sigurd,Schunack, Walter
, p. 317 - 324 (2007/10/02)
3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4.Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6.Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction.Cyclization of the appropiate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection.These primary amines are valuable intermediates for the synthesis of impromidine analogues. Key Words: Homohistamine / Imidazole derivatives / 2-Propenamine derivatives / Impromidine
Diels-Alder Reaction of (E)-4-(2-Nitroethenyl)-1H-imidazoles and Methyl (E)-3-(1-Imidazol-4-yl)propenoates
Kosaka, Keigo,Maruyama, Kazumi,Nakamura, Haruko,Ikeda, Masazumi
, p. 1941 - 1944 (2007/10/02)
Diels-Alder reaction of methyl (E)-3-(1H-imidazol-4-yl)propenoates 2, 3a-c and (E)-4-(2-nitroethenyl)-1H-imidazoles 3d,e with 2,3-dimethyl-1,3-butadiene, cyclopentadiene, and cyclohexa-1,3-diene gave the corresponding cycloadducts 6-9.
