73031-14-8Relevant academic research and scientific papers
Synthesis of acetamide derivatives using S-MWCNT and S-MC as an efficient heterogeneous catalysts
Minchitha,Hareesh,Nagaraju,Kathyayini
, p. 426 - 433 (2017/12/12)
Sulphate modified multiwalled carbon nanotubes (S-MWCNT) and Mesoporous carbon (S-MC) catalysts were prepared by wet impregnation method. These materials were characterized by different analytical techniques such as Powder-XRD, BET surface area analysis, SEM-EDS and TEM analysis to evaluate their bulk and surface properties. Surface acidity of the catalyst was measured by TPD-NH3 technique, as well as n-butyl amine titration. The estimated surface acidity of S-MWCNT and S-MC using n-butyl amine titration was found to be 0.82 and 1.75 mmol/g respectively. The catalytic activity of these materials was investigated in the synthesis of acetamide derivatives using aromatic acids with substituted aromatic amines in a liquid phase reaction. The reaction conditions were optimized to achieve good % yield of the products. In general S-MC catalyst exhibited good catalytic activity and gave higher % yield of the respective acetamides than S-MWCNT. This is attributed to higher surface acidity of S-MC, however the catalyst was found to be non-recyclable. S-MWCNT exhibited moderate % yield and 100% selectivity towards the formation of products. S-MWCNT catalyst was recycled up to 5 times with a consistent % yield of the respective acetamide derivatives. The synthesized acetamide derivatives were analyzed by M.P, 1HNMR techniques.
Discovery of a 3,4,5-trisubstituted-1,2,4-triazole agonist with high affinity and selectivity at the somatostatin subtype-4 (sst4) receptor
Daryaei, Iman,Sandoval, Karin,Witt, Ken,Kontoyianni, Maria,Michael Crider
supporting information, p. 2083 - 2090 (2019/01/04)
A series of compounds containing a 1,2,4-triazole moiety were synthesized, targeting the somatostatin receptor subtype-4 (sst4). Compounds were developed in which the Phe6/Phe7/Phe11, Trp8, and Lys9 mimetic groups were interchanged at positions 3, 4, and 5 of the 1,2,4-triazole ring. The 1,2,4-triazoles containing an 2-(imidazol-4-yl)ethyl substituent at position-3 demonstrated moderate binding affinity at sst4. 1,2,4-Triazoles containing an (indol-3-yl)methyl substituent at position-5 lacked affinity at sst4. The 1,2,4-triazoles containing an aminopropyl group at position-4 showed enhanced binding affinity compared to the 3-position. One compound with an 3-(imidazol-4-yl)propyl group at position-4 (compound 44) imparted high affinity and selectivity at sst4 (sst2A = >10000 nM; sst4 = 19 nM), acting as an agonist (EC50 = 6.8 nM). Docking 44 into a model-built structure of sst4 pointed to differences in its binding versus the other low-affinity compounds and was also in line with one of the two previously reported binding modes. A virtual screening (VS) experiment, employing two separate docking algorithms, was able to score 44 among the top-ranked poses. In summary, compound 44 represents a novel and promising lead structure towards the development of a clinically viable sst4 agonist for the treatment of conditions ranging from Alzheimer's disease to chronic pain.
Aryl substituted amide compounds and its preparation method, pharmaceutical composition containing the same and application thereof (by machine translation)
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Paragraph 0111; 0132; 0133, (2018/07/30)
The invention relates to an aryl-substituted amide compound in the formula (I), a preparing method thereof, a medicine composition comprising the same, and application of the amide compound and the medicine composition to pharmacy, wherein Arl, L1, M1, M2, L2 and Ar2 are defined as in the text. The aryl-substituted amide compound can excite TRPV1 and nuclear receptors (LXRs, PPARs and RXR), adjust expression of cholesterol excretion gap-associated protein ABCA1/G1, SR-BI, adjust expression of inflammation gap-associated protein TNF-alpha and the like, and play roles in promoting excretion of cholesterol and lipid, reducing sugar, adjusting blood lipid, resisting inflammation and reducing blood pressure, and can be used for treating and/or preventing and/or relieving cardiovascular and cerebrovascular diseases, adjusting blood lipid, and resisting atherosclerosis, diabetes mellitus, inflammation, pain and hypertension.
PROCESS FOR THE SYNTHESIS OF IVACAFTOR AND RELATED COMPOUNDS
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Paragraph 039-040; 053, (2016/12/01)
The present patent discloses a novel one pot two-step process for the synthesis of ivacaftor and related compounds of [Formula (I)], wherein R1, R2, R3, R4, R5, R6, R7 and Ar1 are as described above; its tautomers or pharmaceutically acceptable salts thereof starting from indole acetic acid amides.
Dearomatization of Indoles via Palladium-Catalyzed Allylic C-H Activation
Zhang, Heng,Hu, Rong-Bin,Liu, Na,Li, Shi-Xia,Yang, Shang-Dong
supporting information, p. 28 - 31 (2016/01/15)
The first Pd-catalyzed allylic dearomatization of substituted indoles triggered by C-H bond activation is reported. The presence of a catalytic amount of 2,5-DMBQ is proven to be a key factor for the high yield. This one-pot tandem allylic C-H activation/dearomatization sequence provides a straightforward access to 3,3-disubstituted indolines.
Design, synthesis and activity evaluation of some novel indole derivatives
He, Dian,Yang, Zhu-Qing,Hou, Meng
, p. 1729 - 1734 (2015/03/04)
A series of novel indole derivatives as CDK4 inhibitors were designed and synthesized though the condensation reaction between the indolic acid and the corresponding substituted amine. The key step of our synthetic process is the efficient condensation reaction conducted by two different methods. The MTT and kinase assays were conducted used to assess the antitumor activity and cyclin-dependent kinases (CDKs) inhibitory activity. The most active compound 8b has an IC50 of 10-25 μM for the inhibition of four different tumor cells and CDK4. The higher activities of 8b were influenced by more conformational freedom resulted form the non-planar structure and by the stronger hydrogen bonding capability. Thus, the strategy we adapt to design potent, non-toxic CDK4 inhibitors is successful.
Breaking and Making of Rings: A Method for the Preparation of 4-Quinolone-3-carboxylic Acid Amides and the Expensive Drug Ivacaftor
Vasudevan,Jachak, Gorakhnath R.,Reddy, D. Srinivasa
supporting information, p. 7433 - 7437 (2016/01/25)
A simple and convenient method to access 4-quinolone-3-carboxylic acid amides from indole-3-acetic acid amides through one-pot oxidative cleavage of the indole ring followed by condensation (Witkop-Winterfeldt type oxidation) was explored. The scope of the method was confirmed with more than 20 examples and was successfully applied to the synthesis of the drug Ivacaftor, the most expensive drug on the market.
Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines
Islam, Sk Manirul,Ghosh, Kajari,Roy, Anupam Singha,Molla, Rostam Ali
, p. 900 - 907 (2015/02/19)
A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.
Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
supporting information, p. 3683 - 3690 (2014/05/20)
A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade
Zhu, Shaolin,MacMillan, David W. C.
supporting information; experimental part, p. 10815 - 10818 (2012/08/07)
An enantioselective arylation-cyclization cascade has been accomplished using a combination of diaryliodonium salts and asymmetric copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction of pyrroloindolines, an important alkaloid structural motif that is commonly found among biologically active natural products.
