- Compounds with coumarin-biphenyl skeleton, and preparation method and application of compounds
-
The invention belongs to the field of pharmaceutical chemistry, and discloses compounds with a coumarin-biphenyl skeleton, and a preparation method and application of the compounds. The compounds havefollowing structural general formulae. The preparation method of the two compounds is simple and reliable, and the total yield is 40% or above. Preliminary pharmacological experiments show that the compounds have a certain relaxation effect on an in-vitro arterial blood vessel of a rat, and can be used for development of antihypertensive drugs.
- -
-
Paragraph 0038; 0060-0061
(2019/09/14)
-
- Preparation of novel 1,2,3-triazole furocoumarin derivatives via click chemistry and their anti-vitiligo activity
-
The extracts of Psoralea corylifolia?L. were often used for the repigmentation of leukoderma (vitiligo) in traditional Uygur medicine thousands years ago. Nowadays, its active ingredient, furocoumarins, has been clinically applied since it exhibited stron
- Niu, Chao,Lu, Xueying,Aisa, Haji Akber
-
p. 1671 - 1678
(2019/01/24)
-
- Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes
-
Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.
- Lasányi, Dániel,Tolnai, Gergely L.
-
supporting information
p. 10057 - 10062
(2019/12/24)
-
- Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
-
Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.
- Luciani, Lorenzo,Goff, Emily,Lanari, Daniela,Santoro, Stefano,Vaccaro, Luigi
-
supporting information
p. 183 - 187
(2018/01/17)
-
- Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
-
In the present paper 5-[4′-({4-[(4-aryloxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles (5a–g) and [2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl-substituted-1-carbodithioates (11h–q) have been designed and synthesized. These compounds were subjected to docking (against AT1 receptor protein enzyme in complex with Lisinopril), in vitro angiotensin converting enzyme inhibition, anti-proliferative, anti-inflammatory screening (through egg albumin denaturation inhibition and red blood cell membrane stabilization assay) and finally anti-fungal activity analyses. Some of the compounds have shown significant pharmacological properties.
- Kamble, Atulkumar,Kamble, Ravindra,Dodamani, Suneel,Jalalpure, Sunil,Rasal, Vijaykumar,Kumbar, Mahadev,Joshi, Shrinivas,Dixit, Sheshagiri
-
p. 444 - 457
(2017/04/13)
-
- Anti-methicillin resistant Staphylococcus aureus activity, synergism with oxacillin and molecular docking studies of metronidazole-triazole hybrids
-
MRSA causes 60-70% of Staphylococcus aureus infection in hospitals and it has developed resistance against the currently available drugs. Interestingly, a series of 35 metronidazole-triazole hybrids on screening against MRSA were found to be active. Compound 22 was found to be effective at 4 μg/mL concentration against nine strains of MRSA. The inhibitory activity was further enhanced upto 1 μg/mL when this compound was used in combination with oxacillin in 1:1 ratio. All the compounds were found to be non-toxic in THP-1 cell line upto a concentration of 50 μM. The time-kill kinetics studies suggested bacteriostatic nature of the compounds. In silico studies show that these compounds interact with Thr600, Ser598, Asn464, His583 and Tyr446 in the active site of PBP2a crystal structure from MRSA.
- Negi, Beena,Kumar, Deepak,Kumbukgolla, Widuranga,Jayaweera, Sampath,Ponnan, Prija,Singh, Ramandeep,Agarwal, Sakshi,Rawat, Diwan S.
-
p. e426 - e437
(2016/04/19)
-
- Synthesis of Potential Bioactive Novel 7-[2-Hydroxy-3-(1,2,3-triazol-1-yl) propyloxy]-3-alkyl-4-methylcoumarins
-
A series of 50 novel 7-[2-hydroxy-3-(1,2,3-triazol-1-yl)propyloxy]-3-alkyl-4-methylcoumarins had been designed and synthesized in good to excellent yields via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction "click chemistry" of 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarins with variety of acetylene derivatives. In turn, the precursor compound, that is, 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarin, was synthesized by condensation of epichlorohydrin with 7-hydroxy-3-alkyl-4-methylcoumarins followed by opening of the epoxide ring in the resulted 7-epoxymethoxy-3-alkyl-4-methylcoumarins with sodium azide. All the synthesized compounds were unambiguously identified on the basis of their spectral data analyses (IR, 1H-NMR, 13C-NMR spectra, and HRMS).
- Arya, Anu,Kumar, Vinod,Mathur, Divya,Singh, Sukhdev,Brahma, Raju,Singh, Rajpal,Singh, Seema,Sharma,Parmar, Virinder S.,Prasad, Ashok K.
-
-
- A click chemistry strategy to synthesize geraniol-coupled 1,4-disubstituted 1,2,3-triazoles and exploration of their microbicidal and antioxidant potential with molecular docking profile
-
The present paper elicits an unprecedented synthesis of a novel series of 1,2,3-triazole compounds using geraniol as the precursor via 1,3-dipolar cycloaddition using click chemistry strategy. All the synthesized compounds were screened to evaluate their
- Dubey, Nitin,Sharma, Mukesh C.,Kumar, Ashok,Sharma, Pratibha
-
p. 2717 - 2731
(2015/06/22)
-
- Design and synthesis of 2′-Deoxy-2′-[(1,2,3)Triazol-1-Yl]uridines using click chemistry approach
-
A series of novel nucleosides bearing a 1,2,3-triazole moiety at the 2′-position of the sugar moiety has been synthesized starting from 2′-azidouridine and using the copper (I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction. The reactions proceeded in overall yield of 52-82% and gave almost exclusively the 1,4-disubstituted 1,2,3-triazoles. The 2′-azidouridine was synthesized from uridine in two steps, and reacted with a variety of differently substituted alkynes to give the desired 2′-triazole-substituted uridine derivatives.
- Kumar, Surender
-
p. 371 - 378
(2015/05/05)
-
- Isopropanol and potassium tert-butoxide promoted intramolecular direct sp2 C-H functionalization: An expedient synthesis of 1,2,3-triazole annulated chromens and quinolones
-
A series of 1,2,3-triazole annulated chromen and quinolone derivatives have been synthesized by means of direct sp2 C-H functionalization in the presence of iso-propanol and potassium tert-butoxide. The reaction proceeds through homolytic aroma
- Mondal, Biplab,Roy, Brindaban
-
supporting information
p. 6123 - 6127
(2015/10/28)
-
- Practical and metal-free electrophilic aromatic halogenation by interhalogen compounds generated in situ from N-halosuccinimide and catalytic TMSCL
-
Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds. Georg Thieme Verlag Stuttgart New York.
- Maibunkaew, Tapanee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Bunrit, Anon,Ruchirawat, Somsak
-
supporting information
p. 1769 - 1775
(2014/08/05)
-
- Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: Divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
-
The controllable synthesis of 3-methylene-2,3-dihydrobenzofurans 2 and 3-methylene-2,3-dihydroindoles 5 has been developed through Rh-catalyzed intramolecular annulation of aromatic rings with azavinyl carbenes. This journal is
- Tang, Xiang-Ying,Zhang, Yong-Sheng,He, Lv,Wei, Yin,Shi, Min
-
supporting information
p. 133 - 136
(2015/01/09)
-
- Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles
-
A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.
- Smith, Christopher D.,Greaney, Michael F.
-
supporting information
p. 4826 - 4829
(2013/10/08)
-
- Strategies to reduce hERG K+ channel blockade. Exploring heteroaromaticity and rigidity in novel pyridine analogues of dofetilide
-
Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG
- Carvalho, Jo?o F. S.,Louvel, Julien,Doornbos, Maarten L. J.,Klaasse, Elisabeth,Yu, Zhiyi,Brussee, Johannes,Ijzerman, Adriaan P.
-
supporting information
p. 2828 - 2840
(2013/05/22)
-
- Traceless sulfone linker for the solid-phase organic synthesis of 1-(E)-styryl-4-substituted-1,2,3-triazoles
-
A novel, facile, solid-phase, organic synthesis of 1-(E)-styryl-4- substituted-1,2,3-triazoles in good yields and purities via traceless sulfone linker has been developed. Key steps involved in this synthetic procedure include (i) sulfone alkylation of su
- Jiang, Jian-Wen,Sheng, Shou-Ri,Zhang, Xiao-Lan,Fang, Zheng,Cai, Ming-Zhong
-
p. 2784 - 2792
(2013/08/23)
-
- Synthesis of 1,2,3-triazole-fused heterocycles via Pd-catalyzed cyclization of 5-iodotriazoles
-
A convenient approach toward polycyclic frameworks containing fused 1,2,3-triazoles is described. The synthesis consists of a Cu-catalyzed cycloaddition and an intramolecular Pd-catalyzed direct arylation or Heck reaction, and affords the products in good to excellent yields.
- Schulman, Jacqueline M.,Friedman, Adam A.,Panteleev, Jane,Lautens, Mark
-
supporting information; experimental part
p. 55 - 57
(2012/01/05)
-
- Silver(I)-organic networks constructed with flexible silver-ethynide supramolecular synthon o-, m-, p-Cl-C6H5OCH 2C≡C?Agn (n = 4, 5)
-
A series of five silver coordination polymers [(AgL1)·(AgCF 3COO)5·(H2O)3] (1), [(AgL1)2·(AgCF3COO)11·(H 2O)6] (2), [(AgL2)·(AgCF3COO) 3/su
- Li, Bo,Zang, Shuang-Quan,Ji, Can,Mak, Thomas C.W.
-
experimental part
p. 2820 - 2828
(2011/08/09)
-
- Synthesis and antibacterial activity evaluation of metronidazole-triazole conjugates
-
Synthesis and antibacterial activity of metronidazole-triazole conjugates are reported. Total 21 hybrid compounds have been synthesized with different substitution pattern on the triazole ring in order to study their influence on the antibacterial activit
- Beena,Kumar, Nitin,Rohilla, Rajesh K.,Roy,Rawat, Diwan S.
-
scheme or table
p. 1396 - 1398
(2009/11/30)
-
- 1,4-Dihydroindeno[1,2-c]pyrazoles with acetylenic side chains as novel and potent multitargeted receptor tyrosine kinase inhibitors with low affinity for the hERG ion channel
-
The synthesis of a novel series of 1,4-dihydroindeno[1,2-c]pyrazoles with acetylene-type side chains is described. Optimization of those compounds as KDR kinase inhibitors identified 8, which displayed an oral activity in an estradiol-induced murine uterine edema model (ED50 = 3 mg/kg) superior to Sutent (ED50 = 9 mg/kg) and showed potent antitumor efficacy in an MX-1 human breast carcinoma xenograft tumor growth model (tumor growth inhibition = 90% at 25 mg/kg·day po). The compound was docked into a homology model of the homo-tetrameric pore domain of the hERG potassium channel to identify strategies to improve its cardiac safety profile. Systematic interruption of key binding interactions between 8 and Phe656, Tyr652, and Ser624 yielded 90, which only showed an IC50 of 11.6 μM in the hERG patch clamp assay. The selectivity profile for 8 and 90 revealed that both compounds are multitargeted receptor tyrosine kinase inhibitors with low nanomolar potencies against the members of the VEGFR and PDGFR kinase subfamilies.
- Dinges, Jürgen,Albert, Daniel H.,Arnold, Lee D.,Ashworth, Kimba L.,Akritopoulou-Zanze, Irini,Bousquet, Peter F.,Bouska, Jennifer J.,Cunha, George A.,Davidsen, Steven K.,Diaz, Gilbert J.,Djuric, Stevan W.,Gasiecki, Alan F.,Gintant, Gary A.,Gracias, Vijaya J.,Harris, Christopher M.,Houseman, Kathryn A.,Hutchins, Charles W.,Johnson, Eric F.,Li, Hu,Marcotte, Patrick A.,Martin, Ruth L.,Michaelides, Michael R.,Nyein, Michelle,Sowin, Thomas J.,Su, Zhi,Tapang, Paul H.,Xia, Zhiren,Zhang, Henry Q.
-
p. 2011 - 2029
(2008/02/04)
-
- A new series of pyridinyl-alkynes as antagonists of the metabotropic glutamate receptor 5 (mGluR5)
-
Synthesis and some structure-activity relationships for a new series of propargyl ethers as mGluR5 antagonists are reported.
- Bach, Peter,Nilsson, Karolina,Wallberg, Andreas,Bauer, Udo,Hammerland, Lance G.,Peterson, Alecia,Svensson, Tor,Oesterlund, Krister,Karis, David,Boije, Maria,Wensbo, David
-
p. 4792 - 4795
(2007/10/03)
-
- 142. Thermal rearrangements of halogen substituted aryl propargyl ethers
-
7-Chloro-2-chloromethyl-benzofuran (13) and 3, 8-dichloro-2H-1-benzopyran (12) are the main products from the thermal rearrangement (230-260°) of 2, 6-dichlorophenyl propargyl ether (7). Compounds 17, 18 and 19 are also formed, but in much smaller amounts
- Sarcevic, Nada,Zsindely, Janos,Schmid, Hans
-
p. 1457 - 1476
(2007/10/04)
-