56644-06-5Relevant academic research and scientific papers
Transition Metal-Free sp3?sp3 Carbon-Carbon Coupling between Benzylboronic Esters and Alkyl Bromides
Barker, Timothy J.,Russell, Richard W.
supporting information, p. 2782 - 2784 (2021/06/25)
A transition metal-free coupling reaction of benzylboronic esters and alkyl halides has been developed. Both alkyl bromides and alkyl iodides were found to be competent substrates with the nucleophilic boronate intermediate generated from the combination of benzylboronic ester and an alkyllithium. Good chemoselectivity was observed for the reaction with the alkyl bromide in substrates with a second electrophile present. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.
Synthesis of N-ω-phenylalkyl-4-(p-chlorophenyl)-piperidin-4-ol analogues with potent antiproliferative activity against HCT-116 cells
Hatae, Noriyuki,Kujime, Eiko,Yano, Keigo,Kizuka, Mami,Ashida, Rina,Choshi, Tominari,Nishiyama, Takashi,Okada, Chiaki,Iwamura, Tatsunori,Yoshimura, Teruki
, p. 560 - 568 (2019/07/31)
Some opioid analogues, such as morphine and loperamide, were reported to exhibit weak antiproliferative activity against tumor cells. In a study of loperamide analogues, we found that adding an N-ω-phenylalkyl group onto the 4-arylpiperidin-4-ol unit can have important effects on the antiproliferative activity of such compounds against HCT-116 cells. We optimized the distance between the phenyl group and 4-arylpiperidin unit to promote such activity.
Fatty Acid Amide Hydrolase (FAAH), Acetylcholinesterase (AChE), and Butyrylcholinesterase (BuChE): Networked Targets for the Development of Carbamates as Potential Anti-Alzheimer's Disease Agents
Montanari, Serena,Scalvini, Laura,Bartolini, Manuela,Belluti, Federica,Gobbi, Silvia,Andrisano, Vincenza,Ligresti, Alessia,Di Marzo, Vincenzo,Rivara, Silvia,Mor, Marco,Bisi, Alessandra,Rampa, Angela
supporting information, p. 6387 - 6406 (2016/07/26)
The modulation of the endocannabinoid system is emerging as a viable avenue for the treatment of neurodegeneration, being involved in neuroprotective and anti-inflammatory processes. In particular, indirectly enhancing endocannabinoid signaling to therapeutic levels through FAAH inhibition might be beneficial for neurodegenerative disorders such as Alzheimer's disease, effectively preventing or slowing the progression of the disease. Hence, in the search for a more effective treatment for Alzheimer's disease, in this paper, the multitarget-directed ligand paradigm was applied to the design of carbamates able to simultaneously target the recently proposed endocannabinoid system and the classic cholinesterase system, and achieve effective dual FAAH/cholinesterase inhibitors. Among the two series of synthesized compounds, while some derivatives proved to be extremely potent on a single target, compounds 9 and 19 were identified as effective dual FAAH/ChE inhibitors, with well-balanced nanomolar activities. Thus, 9 and 19 might be considered as new promising candidates for Alzheimer's disease treatment.
Suzuki-miyaura cross-coupling reactions of unactivated alkyl halides catalyzed by a nickel pincer complex
Di Franco, Thomas,Boutin, Nicolas,Hu, Xile
, p. 2949 - 2958 (2013/11/06)
A nickel(II) pincer complex, [(MeN2N)Ni-Cl], was used to catalyze alkyl-alkyl and alkyl-aryl Suzuki-Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-borabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane reagents with alkyl halides was achieved in modest to good yields. The reactions tolerated a variety of useful functional groups including ester, ether, furan, thioether, acetal, and Boc groups. Georg Thieme Verlag Stuttgart, New York.
Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides
Yang, Chu-Ting,Zhang, Zhen-Qi,Liu, Yu-Chen,Liu, Lei
, p. 3904 - 3907 (2011/05/15)
Non-activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper-catalyzed cross-coupling with aryl boron compounds and alkyl 9-BBN reagents (see scheme; 9-BBN=9-borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium- and nickel-catalyzed Suzuki-Miyaura coupling reactions of alkyl halides.
Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides
Huo, Shouquan
, p. 423 - 425 (2007/10/03)
(Matrix presented) Alkylzinc bromides have been efficiently prepared by the direct insertion of zinc metal (dust, powder, granule, shot), activated with 1-5 mol % I2, into alkyl bromides in a polar aprotic solvent. The zinc reagents thus formed undergo Ni- and Pd-catalyzed cross-coupling with aryl halides to produce functionalized alkylarenes in excellent yields.
The Synthesis of Medium-Sized Cyclic Lactams by the Intramolecular Friedel-Crafts Cyclization of Isocyanates. Formation of Novel Pyrazolobenzolactams
Butler, Donald E.,Alexander, Susan M.
, p. 1173 - 1177 (2007/10/02)
A series of 4-ω-phenylalkyl substituted-1H-pyrazol-5-amines has been synthesized from the corresponding α-acetylphenylalkanenitriles and methylhydrazine.They were converted into the corresponding 5-isocyanates and cyclized under Friedel-Crafts conditions
