1664-40-0Relevant articles and documents
Salts of 2- or 3-haloalkylamines in the synthesis of N-aminoalkyl derivatives of heterocyclic and aromatic amines
Vasilyeva,Vorobyeva,Osipov
, p. 2211 - 2215 (2016)
Reactions of 2-haloethyl- or 3-halopropylamine salts with NH-substrates (indoline, 1,2,3,4-tetrahydroquinoline, aniline, and N-ethylaniline) in the presence of NaHCO3 in water furnished various N-aminoalkyl derivatives of heterocyclic and aromatic amines.
Design, synthesis and evaluation of γ-turn mimetics as LSD1-selective inhibitors
Ota, Yosuke,Miyamura, Shin,Araki, Misaho,Itoh, Yukihiro,Yasuda, Shusuke,Masuda, Mitsuharu,Taniguchi, Tomoyuki,Sowa, Yoshihiro,Sakai, Toshiyuki,Itami, Kenichiro,Yamaguchi, Junichiro,Suzuki, Takayoshi
, p. 775 - 785 (2018)
Lysine-specific demethylase 1 (LSD1) is an attractive molecular target for cancer therapy. We have previously reported potent LSD1-selective inhibitors (i.e., NCD18, NCD38, and their analogs) consisting of trans-2-phenylcyclopropylamine (PCPA) or trans-2-arylcyclopropylamine (ACPA) and a lysine moiety that could form a γ-turn structure in the active site of LSD1. Herein we report the design, synthesis and evaluation of γ-turn mimetic compounds for further improvement of LSD1 inhibitory activity and anticancer activity. Among a series of γ-turn mimetic compounds synthesized by a Mitsunobu-reaction-based amination strategy, we identified 1n as a potent and selective LSD1 inhibitor. Compound 1n induced cell cycle arrest and apoptosis through histone methylation in human lung cancer cells. The γ-turn mimetics approach should offer new insights into drug design for LSD1-selective inhibitors.
Design and synthesis of new potent 5-HT7 receptor ligands as a candidate for the treatment of central nervous system diseases
Drabczyk, Anna K.,Ja?kowska, Jolanta,Ku?aga, Damian,Latacz, Gniewomir,Pla?uk, Damian,Rózga, Karolina,Sata?a, Grzegorz
supporting information, (2021/10/29)
Owing to their multifunctional pharmacological profiles (including dual 5-HT1A/5-HT7 action), arylpiperazine derivatives are widely used for treating central nervous system diseases including the depression or neuropathic pain. Herein we describe the design, synthesis and evaluation of biological activity of novel 5-HT7 ligands derived of 2,4,6-triamino-1,3,5-triazine. The studied compounds showed affinity and high selectively towards 5-HT7 receptor with the two most active compounds 34 (Ki = 61 nM), 22 (Ki = 109 nM) showing good metabolic stability and moderate affinity to CYP3A4 isoenzyme. Compound 22 had high hepatotoxicity at a concentration below 50 μM, while compound 34 showed low hepatotoxicity even at a concentration above 50 μM.
Phosphorescent Cyclometalated Platinum(II) Imidazolinylidene Complexes
Stipurin, Sergej,Strassner, Thomas
, p. 804 - 813 (2021/02/05)
We present the synthesis and characterization of six novel bidentate (Formula presented.) cyclometalated platinum(ii) complexes derived from saturated N-heterocyclic carbene precursors, namely 1-aryl-3-methyl-1H-4,5-dihydroimidazolium salts. The title compounds were then synthesized by a multi-step reaction, which includes an in situ generation of the silver carbene complex, followed by transmetalation to platinum and subsequent introduction of the β-diketonate ligand. Structural characterization by NMR experiments and solid-state structures prove the cyclometalation and the saturated backbone of the NHC motif. Photophysical and electrochemical properties of the platinum(ii) complexes were examined and studied in detail by DFT calculations. The title compounds are strongly emissive at room temperature in the sky-blue region of the visible spectrum and show quantum yields of up to 71 % in a PMMA matrix.
A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events
Beard, Matthew C.,Chen, Xihan,Han, Chuang,Lin, Yixiong,Martin, Jovan San,Miller, Collin,Wang, Xiaoming,Yamamoto, Nobuyuki,Yan, Yanfa,Yan, Yong,Yazdi, Sadegh,Zeng, Xianghua
supporting information, p. 11361 - 11369 (2021/08/16)
Heterogeneous photocatalysis is less common but can provide unique avenues for inducing novel chemical transformations and can also be utilized for energy transductions, i.e., the energy in the photons can be captured in chemical bonds. Here, we developed a novel heterogeneous photocatalytic system that employs a lead-halide perovskite nanocrystal (NC) to capture photons and direct photogenerated holes to a surface bound transition metal Cu-site, resulting in a N-N heterocyclization reaction. The reaction starts from surface coordinated diamine substrates and requires two subsequent photo-oxidation events per reaction cycle. We establish a photocatalytic pathway that incorporates sequential inner sphere electron transfer events, photons absorbed by the NC generate holes that are sequentially funneled to the Cu-surface site to perform the reaction. The photocatalyst is readily prepared via a controlled cation-exchange reaction and provides new opportunities in photodriven heterogeneous catalysis.
Method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide
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Paragraph 0029-0035; 0160; 0132; 0133; 0162, (2019/01/14)
The invention discloses a method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide. That is to say, the alkyl halide or the arylhalide and organic amine are mixed according to a certain ratio, and under light irradiation, C-N coupling reaction is carried out, so that a corresponding target product is generated for preparing the secondary amine or the tertiary amine. Compared with existing synthesis technologies, the method has the advantages that the aryl halide or the alkyl halide which is cheap and easy to get is selected as a reaction substrate, the method has good universality for different organic amine separately, moreover, the product selectivity is high, and separation and purification are easy; moreover, the synthesis method does not need to be conducted under severe conditions of high temperature and the like, a green and sustainable light source is adopted as driving force, the atom economy is high, andthe method has wide application prospects.
Naphthalene dianhydride based selective detection targetable fluorescent probe for monitoring exogenous Iron in living cells
Rohini, Gandhaveeti,Ramaiah, Konakanchi,Sreekanth, Anandaram
supporting information, p. 3858 - 3862 (2018/09/25)
A green emissive PET operating fluorescent turn-on cell permeable novel probe R1 has been successfully developed and utilized for the detection of Fe+3 in the pure aqueous system at sub-nanomolar level. Moreover, probe R1 demonstrate highly sensitive and selective towards Fe+3 over the other divalent and trivalent metal ions and was established by using fluorescence spectroscopy. The efficiency and aid of R1 was demonstrated by the fluorescence imaging of captured Fe+3 within Pollen grains by using fluorescence microscopy. These results indicate that, this is the first fluorescent turn-on PET probe to detect sub-nanomolar Fe+3 in the pure aqueous system and in cellular level.
COMPOUND HAVING γ TURN STRUCTURE AND LSD1 INHIBITOR USING THE SAME
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Paragraph 0185-0190, (2017/12/27)
PROBLEM TO BE SOLVED: To provide a compound having LSD1 inhibitory activity and cancer cell growth inhibitory effect. SOLUTION: There is provided a compound represented by the formula (1) and a salt thereof. (1), where R1 is an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group or a heteroaryl group, R2 is H, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group, R3 is H, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group or a heteroaryl group, R4 is an aryl group or a heteroaryl group, each of the above described groups may be substituted, n is an integer of 2 to 10 and *1 and *2 are asymmetric carbons. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives
Lv, Kai,Li, Linhu,Wang, Bo,Liu, Mingliang,Wang, Bin,Shen, Weiyi,Guo, Huiyuan,Lu, Yu
, p. 117 - 125 (2017/06/05)
We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.
Cu2O/nano-CuFe2O4: An efficient and magnetically recoverable catalyst for the ligand-free N-arylation of amines and nitrogen heterocycles with aryl halides
Elhampour, Ali,Nemati, Firouzeh,Kaveh, Mahdieh
supporting information, p. 223 - 225 (2016/03/01)
An efficient strategy has been developed for the N-arylation of azoles and aliphatic amines with aryl halide using a Cu2O/nano-CuFe2O4 magnetic composite as the catalyst and KOH as the base. The methodology is found to be applicable to a variety of nitrogen-containing heterocycles, such as imidazole, indole, and pyrrole, as well as aliphatic amines in high yields with practical simplicity under cost-effective "ligand-free" conditions. The magnetic property of the catalyst allowed its fast separation from the reaction medium by an external magnet. Additionally, the inexpensive catalyst could be recycled for five consecutive runs with small drops in catalytic activity.