7250-19-3Relevant academic research and scientific papers
ISOQUINOLINE DERIVATIVES AS PROTEIN KINASE INHIBITORS
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, (2021/02/12)
The present invention relates to a compound suitable for use as a kinase inhibitor
Design, synthesis, antimicrobial evaluation, and molecular docking of novel chiral urea/thiourea derivatives bearing indole, benzimidazole, and benzothiazole scaffolds
Lafzi, Ferruh,Kilic, Deryanur,Yildiz, Melike,Saracoglu, Nurullah
, (2021/05/27)
Urea/thiourea derivatives with heteroaromatic scaffolds such as indole, benzimidazole, and benzothiazole were designed, synthesized, and evaluated for their potential antimicrobial activity in vitro assays to establish against B. cereus, S. aureus, E. coli, and P. aeruginosa. Our results indicate that compounds are only active in gram-positive bacteria. Molecular docking studies were carried out for the most efficient compounds to understand the interactions with proteins involved in peptidoglycan synthesis. ADME calculations indicate that these compounds are more likely to be taken via the oral route. In summary, these findings may contribute to the design and development of candidates for more effective therapeutics in biological systems.
First-Row Transition Metal and Lithium Pyridine-ene-amide Complexes Exhibiting N- and C-Isomers and Ligand-Based Activation of Benzylic C-H Bonds
Lindley, Brian M.,Wolczanski, Peter T.,Cundari, Thomas R.,Lobkovsky, Emil B.
supporting information, p. 4656 - 4668 (2015/10/28)
Ene-amines Z-3-(2-pyridyl)-1-aza(2,6-iPr2-Ph)propene, (pynac)H, and 2-(2-pyridyl)-1-aza(2,6-R,R′-Ph)propene, (pyEA-ArRR′)H, were synthesized by condensation procedures; corresponding lithium or potassium ene-amides were prepared via standard deprotonation protocols. Addition of 2 equiv of (pynac)H to {(Me3Si)2N}2Fe(THF) or 2 Li(pynac) to FeBr2(THF)2 afforded (pynac)2Fe (1), while treatment of CrCl2(THF)2, MnCl2, FeBr2(THF)2, and CoCl2py4 with 2 equiv of (pyEA-AriPr2)K afforded pseudotetrahedral (pyEA-AriPr2)2M (2-M, M = Cr, Mn, Fe) and (pyEA-AriPr2)2Co-py (2-Co-py). Diamagnetic (κ-C,N-pyEA-AriPr2)3Co (3) was prepared in low yield (～7%) from CoCl2, and its Co-C(sp3) linkages are unusually low in field strength. Reactivity studies yielded little clean reactivity, but thermolysis of 2-Co-py afforded the bis-indolamide derivative {κ-N,N-N(C6H3(2-iPr)CMe2C(Me)(2-py)}2Co (5-Co), and related thermolyses of 2-M (M = Cr, Mn, Fe), conducted on NMR tube scales, generated related 5-M (M = Cr, Mn, Fe) at roughly the same rates. This observation prompted thermolyses of (pyEA-ArRR′)Li, which rearrange to their corresponding indolamides in >90% yields. Rate studies, accompanied by KIE and EIE observations, revealed that an initial hydrogen transfer is reversible and is likely to correspond to an anionic rearrangement, whereas C-C bond formation is rate-determining, as suggested by accompanying calculations. X-ray structure determinations of 1, 2-Fe, 2-Co-py, 3, and 5-Co were conducted.
The first isocyanide of plant origin expands functional group diversity in cruciferous phytoalexins: Synthesis, structure and bioactivity of isocyalexin A
Pedras, M. Soledade C.,Yaya, Estifanos E.
supporting information; experimental part, p. 3613 - 3616 (2012/06/18)
Although isocyanides are not rare amongst terrestrial microbes and marine organisms, despite tens of thousands of natural products isolated from plants, isocyanides are still missing. Isocyalexin A is the first isocyanide of plant origin. Isocyalexin A was isolated from UV-irradiated rutabaga roots and shown to be a new cruciferous phytoalexin. Its chemical structure was proven by analysis of NMR spectroscopic data and chemical synthesis.
Three-component reaction involving metal-free heteroannulation of N-Boc-3-amido indole, aryl aldehydes, and aromatic alkynes under microwave conditions: Synthesis of highly diversified δ-carbolines
Sharma, Sudhir K.,Mandadapu, Anil K.,Saifuddin, Mohammad,Gupta, Sahaj,Agarwal, Piyush K.,Mandwal, Ashok K.,Gauniyal, Harsh M.,Kundu, Bijoy
experimental part, p. 6022 - 6024 (2010/11/18)
An efficient synthesis toward highly diversified δ-carbolines via one-pot multicomponent reaction using N-Boc-3-amido indoles, aryl aldehydes, and aromatic terminal alkynes under microwave conditions has been described.
Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines
Bahekar, Rajesh H.,Jain, Mukul R.,Goel, Ashish,Patel, Dipam N.,Prajapati, Vijay M.,Gupta, Arun A.,Jadav, Pradip A.,Patel, Pankaj R.
, p. 3248 - 3265 (2008/02/07)
Sulfonylureas stimulate insulin secretion independent of the blood glucose concentration and therefore cause hypoglycemia in type 2 diabetic patients. Over the last years, a number of aryl-imidazoline derivatives have been identified that stimulate insulin secretion in a glucose-dependent manner. In the present study, we have developed three series of substituted N-(thieno[2,3-b]pyridin-3-yl)-guanidine (2a-l), N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidine (3a-l), and N-(1H-indol-3-yl)-guanidine (4a-l) as new class of antidiabetic agents. In vitro glucose-dependent insulinotropic activity of test compounds 2a-l, 3a-l, and 4a-l was evaluated using RIN5F (Rat Insulinoma cell) based assay. All the test compounds showed concentration-dependent insulin secretion, only in presence of glucose load (16.7 mmol). Some of the test compounds (2c, 3c, and 4c) from each series were found to be equipotent to BL 11282 (standard aryl-imidazoline), which indicated that the guanidine group acts as a bioisostere of imidazoline ring system.
Synthesis of Substituted Indolobenzodiazepine Derivatives
Hiremath, Shivayogi P.,Hiremath, Dakshayani M.,Purohit, Muralidhar G.
, p. 930 - 933 (2007/10/02)
Various substituted-7,12-dihydroindolobenzodiazepines (4a-e) have been prepared from the corresponding 3-aminoindoles (1a-e) through Ullmann reaction with o-chloroaniline, acylation of the resulting 3-(o-aminophenylamino)indoles (2a-e) and cyclization of amides (3a-e) with POCl3.Similar systems have also been synthesized from ethyl 3-bromoindole-2-carboxylates (6a-e).The bromo esters react with o-phenylenediamine to give ethyl 3-(o-aminophenylamino)indole-2-carboxylates (7a-e) which undergo cyclization in the presence of PPA to yield 5,6,7,12-tetrahydroindolobenzodiazepin-6-ones (8a-e).
Synthesis of 3-Aminoindoles & Ethyl Pyrroloindole-2-carboxylates
Hiremath, S. P.,Kaddargi, S. S.,Mruthyunjayaswamy, H. M.,Purohit, M. G.
, p. 767 - 769 (2007/10/02)
Various indoles (1a-g) on nitrosation with sodium nitrite and acetic acid yield the corresponding 3-nitrosoindoles (2a-g).These on reduction with sodium dithionate, in the presence of 2 N NaOH, afford 3-aminoindoles (3a-g) in good yields.Coupling of a diazotised solution of 3a-g with ethyl α-methylacetoacetate (5) yields the respective ethyl indol-3-ylpyruvate hydrazones (6a-g) which on Fischer indolization with alcoholic H2SO4 give various ethyl pyrroloindole-2-carboxylates (7a-g).
