2629-72-3Relevant academic research and scientific papers
A general synthesis of alkylpyridines
Iglesias, Beatriz,Alvarez, Rosana,De Lera, Angel R
, p. 3125 - 3130 (2001)
The hydroboration of alkenes, followed by the coupling of the B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with bromopyridines constitutes an efficient procedure for the attachment of functionalized alkyl chains to the pyridine nucleus.
Influence of Sulfoxide Group Placement on Polypeptide Conformational Stability
Gharakhanian, Eric G.,Bahrun, Ehab,Deming, Timothy J.
supporting information, p. 14530 - 14533 (2019/10/02)
The synthesis of a homologous series containing five new nonionic sulfoxide containing polypeptides was described. Sulfoxide groups bestowed water solubility for all homologues, which allowed their use as a model for study of helix-coil transitions in water while avoiding contributions from charged groups or phase separation. Polypeptides were found to adopt chain conformations in water that were dependent on distance of sulfoxides from chain backbones, overall side-chain lengths, and solvent. These results allow preparation of polypeptide segments with different chain conformations without changing chemical functionality for potential use in structural studies and functional applications.
Derivative of Kutkin dimer analog JJA-D0 or its pharmaceutically acceptable salt, preparation method and use thereof
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Paragraph 0111-0112, (2019/01/08)
The invention relates to a derivative of Kutkin dimer analog JJA-D0 or its pharmaceutically acceptable salt, a preparation method and use thereof. The compound has a structure shown as a general formula (I). According to the invention, an alkyl group, an aryl group, a heteroaryl group, an alkoxycarbonylalkyl group, an acyl group, a sulfonate group, an antioxidant group such as a lipoic acid group,a H2S donor group such as a cysteine group, and a NO donor group such as a nitrate group are introduced to JJA-D0, and a series of structurally novel compounds can be synthesized and disclosed. The compounds inhibit NADPH oxidase and have superior anti-oxidation and anti-inflammatory pharmacological mechanisms by comparing with Kutkin, the compounds also have donor groups that provide NO and H2S,can further enhance pharmacological activity, and can be a new class of multifunctional compounds. The disclosed JJA-D0 derivative can be used for preparing health products or drugs for prevention ortreatment of diseases associated with NADPH oxidase, diseases associated with free radicals, diseases associated with inflammation, diseases associated with NO, and diseases associated with H2S.
Practical Intermolecular Hydroarylation of Diverse Alkenes via Reductive Heck Coupling
Gurak, John A.,Engle, Keary M.
, p. 8987 - 8992 (2018/09/11)
The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of aliphatic and heteroatom-substituted terminal alkenes and select internal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective with terminal alkenes and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications are demonstrated. Mechanistic experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.
HYDROXYL PURINE COMPOUNDS AND USE THEREOF
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Paragraph 0342; 0344, (2018/04/05)
Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers thereof or pharmaceutically acceptable salts thereof.
A step-by-step crystallization for preparing thio alkyl/alkenyl cysteine sulfoxide method
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Paragraph 0065; 0066, (2017/05/26)
The invention discloses a method for preparing thioalkyl/alkenyl cysteine sulfoxide by fractional crystallization, belonging to the technical field of compound preparation. The method comprises the following steps: adding cysteine or cysteine salts, a sodium hydroxide solution and an R group (alkyl or alkenyl)-derived material into absolute ethanol in sequence for reaction to synthesize coarse ACSs, re-crystallizing ACSs, purifying, oxidizing to form ACSOs, and fractionally crystallizing to obtain natural dextrorotatory ACSOs, wherein the R group-derived material is replaced to synthesize different types of ACSOs in allium; enantiomers in racemes are separated by adopting the fractional crystallization method to obtain natural dextrorotatory ACSOs with optical activity. Compared with a conventional extraction method, the method has the characteristics that the yield and the purity are high, a conventional complicated extraction process is avoided, the product has the optical activity, and the physical property is close to that of natural extract; the product is used in the fields of health products, pharmaceuticals and the like, the effects of resisting bacteria and cancers, reducing blood fat and the like of ACSOs are brought into play, or the product serves as an intermediate such as an active ingredient-diallyl thiosulfinate for synthesizing allium.
New 13-pyridinealkyl berberine analogues intercalate to DNA and induce apoptosis in HepG2 and MCF-7 cells through ROS mediated p53 dependent pathway: Biophysical, biochemical and molecular modeling studies
Chatterjee, Sabyasachi,Mallick, Sumana,Buzzetti, Franco,Fiorillo, Gaetano,Syeda, Tanjia Monir,Lombardi, Paolo,Saha, Krishna Das,Kumar, Gopinatha Suresh
, p. 90632 - 90644 (2015/11/11)
A new series of 13-pyridinealkyl berberine analogues was synthesized and their DNA binding efficacy studied by employing spectroscopic, calorimetric and molecular modeling techniques. Analogues with more than one CH2 group showed better intercalative binding than berberine. The analogue with one CH2 group bound DNA weaker than berberine. The binding of the analogue with single CH2 group was entropy driven, while those with more than one CH2 group was favoured by both entropy and enthalpy changes. Higher salt concentration and temperature destabilized the binding. A larger contribution from non-polyelectrolytic forces to the Gibbs energy and the involvement of strong hydrophobic interactions were inferred. Molecular modeling pin pointed the specific binding site and the non-covalent interactions in the association. The best DNA binding analogue (BER5) inhibited the growth of hepatocellular and breast carcinoma most efficiently. It induced apoptosis in HepG2 and MCF-7 cells with externalization of phosphatidylserine and reactive oxygen species generation with accumulation of cells in the G0/G1 phase. Furthermore, up regulation of p53 and p21 indicated the role of p53 in BER5 mediated apoptosis. The results suggested that 13-pyridinealkyl berberine analogues intercalated to DNA much stronger than berberine, the chain length of the linker plays an important role for the binding, and they induced ROS mediated apoptosis in HepG2 and MCF-7 cells by p53 modulation.
The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure-activity relationships
Shaghafi, Michael B.,Barrett, David G.,Willard, Francis S.,Overman, Larry E.
supporting information, p. 1031 - 1036 (2014/03/21)
We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3- arylhexahydropyrrolo[1,2-c]pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner.
PROCESS FOR THE PREPARATION OF 3-(4-PYRIDINYL)-PROPANOL AND INTERMEDIATES USEFUL IN ITS SYNTHESIS
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Page/Page column 10-11, (2011/11/30)
A process for the preparation of 3-(4-pyridinyl)-propanol or a salt thereof and intermediates useful in its synthesis.
Efficient S-alkylation of cysteine in the presence of 1,1,3,3- tetramethylguanidine
W?ostowski, Marek,Czarnocka, Sylwia,MacIejewski, Piotr
experimental part, p. 5977 - 5979 (2010/11/21)
The synthesis of S-alkylated cysteine derivatives was carried out successfully in the presence of 1,1,3,3-tetramethylguanidine. Alkylation proceeded in high yields on unprotected amino acids and peptides containing a sulfhydryl group.
