106918-32-5Relevant academic research and scientific papers
One-carbon homologation of pyrrole carboxaldehyde via wittig reaction and mild hydrolysis of vinyl ether - Toward the synthesis of a sterically locked phytochrome chromophore
Sakata, Ryo,Soeta, Takahiro,Ukaji, Yutaka
, p. 593 - 603 (2015)
Mild hydrolysis of vinyl ether derived from a pyrrole carboxaldehyde corresponding to the B,C-ring component of phytochromobilin chromophore was achieved by treatment with oxalyl chloride in chloroform in the presence of water and ethanol to afford a one-carbon homologated aldehyde. This aldehyde was applied to the synthesis of the sterically locked 15E-anti CD-ring component of the chromophore. Furthermore, the aldehyde could be converted to the intermediate for the sterically locked 5Z-anti AB-ring component.
TLR2 MODULATOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
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Paragraph 001299-001300, (2021/12/08)
The present disclosure relates to compounds which modulate the activity of Toll-like receptor (TLR) proteins, including agonists or activators, partial agonists, and antagonists. Of particular interest of compounds that modulate the activity of TLR2, as well as methods of using such compounds to treat cancer and other disorders associated with a TLR2 pathway.
Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding
Zhu, Zixi,Glinkerman, Christopher M.,Boger, Dale L.
supporting information, p. 20778 - 20787 (2020/12/22)
An unprecedented 1,4-cycloaddition (vs 3,6-cycloaddition) of 1,2,4,5-tetrazines is described with preformed or in situ generated aryl-conjugated enamines promoted by the solvent hydrogen bonding of hexafluoroisopropanol (HFIP) that is conducted under mild reaction conditions (0.1 M HFIP, 25 °C, 12 h). The reaction constitutes a formal [4 + 2] cycloaddition across the two nitrogen atoms (N1/N4) of the 1,2,4,5-tetrazine followed by a formal retro [4 + 2] cycloaddition loss of a nitrile and aromatization to generate a 1,2,4-triazine derivative. The factors that impact the remarkable change in the reaction mode, optimization of reaction parameters, the scope and simplification of its implementation through in situ enamine generation from aldehydes and ketones, the reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, a survey of participating 1,2,4,5-tetrazines, and key mechanistic insights into this reaction are detailed. Given its simplicity and breath, the study establishes a novel method for the simple and efficient one-step synthesis of 1,2,4-triazines under mild conditions from readily accessible starting materials. Whereas alternative protic solvents (e.g., MeOH vs HFIP) provide products of the conventional 3,6-cycoladdition, the enhanced hydrogen bonding capability of HFIP uniquely results in promotion of the unprecedented formal 1,4-cycloaddition. As such, the studies represent an example of not just an enhancement in the rate or efficiency of a heterocyclic azadiene cycloaddition by hydrogen bonding catalysis but also the first to alter the mode (N1/N4 vs C3/C6) of cycloaddition.
CINNOLINE DERIVATIVES USEFUL AS CB-1 RECEPTOR INVERSE AGONISTS
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Page/Page column 81; 82, (2016/08/10)
The present invention is directed to cinnoline derivatives of formula (I) pharmaceutical compositions containing them and their use in the treatment of disorders and conditions mediated by the CB-1 receptor; more particularly, use in the treatment of disorders and conditions responsive to inverse agonism of the CB-1 receptor. More particularly, the compounds of the present invention are useful in the treatment of metabolic disorders.
CHEMICAL COMPOUNDS
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, (2015/11/11)
The present invention provides a compound of a formula (I): or a pharmaceutically acceptable salt thereof; a process for preparing such a compound; and to the use of such a compound in the treatment of an ENaC mediated disease state (such as asthma, CF or COPD).
A straightforward organocatalytic alkylation of 2-arylacetaldehydes: An approach towards bisabolanes
Gualandi, Andrea,Canestrari, Pietro,Emer, Enrico,Cozzi, Pier Giorgio
supporting information, p. 528 - 536 (2014/05/20)
A highly stereoselective organocatalytic aalkylation of 2-arylacetaldehydes with a commercially available carbenium tetrafluoroborate is described. The stereoselective alkylation was carried out in acetonitrile/ water, under air in the presence of a commercially available imidazolidinone (MacMillan's catalyst). Key intermediates for the synthesis of bisabolanes were obtained through a simple chemistry. In particular a direct, enantioselective and facile synthesis of (R)-(-)-curcumene is described.
Structure-based design of novel potent protein kinase CK2 (CK2) inhibitors with phenyl-azole scaffolds
Hou, Zengye,Nakanishi, Isao,Kinoshita, Takayoshi,Takei, Yoshinori,Yasue, Misato,Misu, Ryosuke,Suzuki, Yamato,Nakamura, Shinya,Kure, Tatsuhide,Ohno, Hiroaki,Murata, Katsumi,Kitaura, Kazuo,Hirasawa, Akira,Tsujimoto, Gozoh,Oishi, Shinya,Fujii, Nobutaka
supporting information; experimental part, p. 2899 - 2903 (2012/06/01)
Protein kinase CK2 (CK2) is a ubiquitous serine/threonine protein kinase for hundreds of endogenous substrates. CK2 has been considered to be involved in many diseases, including cancers. Herein we report the discovery of a novel ATP-competitive CK2 inhibitor. Virtual screening of a compound library led to the identification of a hit 2-phenyl-1,3,4-thiadiazole compound. Subsequent structural optimization resulted in the identification of a promising 4-(thiazol-5-yl)benzoic acid derivative.
Synthesis and evaluation of a γ-lactam as a highly selective EP2 and EP4 receptor agonist
Xiao, Yufang,Araldi, Gian Luca,Zhao, Zhong,Reddy, Adulla,Karra, Srinivasa,Brugger, Nadia,Fischer, David,Palmer, Elizabeth,Bao, Bagna,Mckenna, Sean D.
, p. 821 - 824 (2008/09/18)
γ-Lactam analogs (2) of EP4 receptor agonists were identified by substitution of the pyrazolidinone ring (1) with a pyrrolidinone ring. Several compounds (such as 2a, 2h) with high potency, selectivity and acceptable PK profiles were discovered. These were assessed in animal models of ovulation induction and bronchoconstriction.
The mechanism for the rhodium-catalyzed decarbonylation of aldehydes: A combined experimental and theoretical study
Fristrup, Peter,Kreis, Michael,Palmelund, Anders,Norrby, Per-Ola,Madsen, Robert
, p. 5206 - 5215 (2008/12/22)
The mechanism for the rhodium-catalyzed decarbonylation of aldehydes was investigated by experimental techniques (Hammett studies and kinetic isotope effects) and extended by a computational study (DFT calculations). For both benzaldehyde and phenyl acetaldehyde derivatives, linear Hammett plots were obtained with positive slopes of +0.79 and +0.43, respectively, which indicate a buildup of negative charge in the selectivity-determining step. The kinetic isotope effects were similar for these substrates (1.73 and 1.77 for benzaldehyde and phenyl acetaldehyde, respectively), indicating that similar mechanisms are operating. A DFT (B3LYP) study of the catalytic cycle indicated a rapid oxidative addition into the C(O)-H bond followed by a rate-limiting extrusion of CO and reductive elimination. The theoretical kinetic isotope effects based on this mechanism were in excellent agreement with the experimental values for both substrates, but only when migratory extrusion of CO was selected as the rate-determining step.
Activated iodosylbenzene monomer as an ozone equivalent: Oxidative cleavage of carbon-carbon double bonds in the presence of water
Miyamoto, Kazunori,Tada, Norihiro,Ochiai, Masahito
, p. 2772 - 2773 (2007/10/03)
Reported here for the first time are the developments of an efficient method for oxidative cleavage of carbon-carbon double bonds yielding carbonyl compounds by using aryl-λ3-iodanes, which involve a combination of iodosylbenzene and HBF4 in the presence of water. The method serves as a safety alternative to ozonolysis. The oxidative cleavage of olefins probably involves the hitherto unknown direct vicinal dihydroxylations of double bonds with aryl-λ3-iodanes and the subsequent oxidative glycol fissions. Cyclic (cyclopentenes, cyclohexenes, etc.) and acyclic olefins are cleaved smoothly under our conditions. In the reaction of electron-deficient styrenes such as m-nitrostyrene, intermediate formation of the corresponding epoxide was detected. A variety of aryloxiranes also undergo an oxidative cleavage of the epoxide rings under our conditions, and aromatic aldehydes were obtained in good yields. Copyright
