1753-75-9Relevant academic research and scientific papers
Bisthienylethenes containing a benzothiadiazole unit as a bridge: Photochromic performance dependence on substitution position
Zhu, Weihong,Meng, Xianle,Yang, Yuheng,Zhang, Qiong,Xie, Yongshu,Tian, He
, p. 899 - 906 (2010)
A conveniently synthesized photochromic compound, BTB-1, containing an unprecedented six-mem- bered 2, 1, 3-benzothiadiazole unit as the center ethene bridge, possesses good photochromic performance, with a high cyclization quantum yield and moderate fatigue resistance in solution or an organogel system. The fluorescence of BTB-1 can be modulated by solvato- and photochromism. However, the analogue BTB-2, in which the di- methylthiophene substituents are relocated to the 5, 6-positions of benzothia- diazole, does not show any detectable photochromism. To the best of our knowledge, this is the first example of six-membered bridge bisthienylethenes (BTEs) in which the photochromism can be controlled by the substitution position. The photochromism difference is elucidated by the analysis of resonance structure, the Woodward- Hoffmann rule, and theoretical calculations on the ground-state potential- energy surface. In a well-ordered single-crystal state, BTB-1 adopts a relatively rare parallel conformation, and forms an interesting two-dimensional structure due to the presence of multiple directional intermolecular interactions, including C-H-N and C-H-S hydrogen-bonding interactions, and π stacking interactions. This work contributes to several aspects for developing novel photochromic BTE systems with fluorescence modulation and performances controlled by substitution position in different states (solution, or- ganogel, and single crystal).
Synthesis, Antiviral Activity, and Structure–Activity Relationship of 1,3-Benzodioxolyl Pyrrole-Based Entry Inhibitors Targeting the Phe43 Cavity in HIV-1 gp120
Curreli, Francesca,Belov, Dmitry S.,Ahmed, Shahad,Ramesh, Ranjith R.,Kurkin, Alexander V.,Altieri, Andrea,Debnath, Asim K.
, p. 2332 - 2348 (2018/10/26)
The pathway by which HIV-1 enters host cells is a prime target for novel drug discovery because of its critical role in the life cycle of HIV-1. The HIV-1 envelope glycoprotein gp120 plays an important role in initiating virus entry by targeting the primary cell receptor CD4. We explored the substitution of bulky molecular groups in region I in the NBD class of entry inhibitors. Previous attempts at bulky substituents in that region abolished antiviral activity, even though the binding site is hydrophobic. We synthesized a series of entry inhibitors containing the 1,3-benzodioxolyl moiety or its bioisostere, 2,1,3-benzothiadiazole. The introduction of the bulkier groups was well tolerated, and despite only minor improvements in antiviral activity, the selectivity index of these compounds improved significantly.
Funnel shaped molecules containing benzo/pyrido[1,2,5]thiadiazole functionalities as peripheral acceptors for organic photovoltaic applications
Paramasivam, Mahalingavelar,Gupta, Akhil,Babu, N. Jagadeesh,Bhanuprakash,Bhosale, Sheshanath V.,Rao, V. Jayathirtha
, p. 66978 - 66989 (2016/07/30)
A series of four novel funnel shaped triphenylamine core derivatized materials with various combinations of 3,6-di-tert-butyl-9H-carbazole as donors and benzo/pyrido[1,2,5]thiadiazole as peripheral acceptors were designed, synthesized and characterized. O
Aromaticity-controlled thermal stability of photochromic systems based on a six-membered ring as ethene bridges: Photochemical and kinetic studies
Yang, Yuheng,Xie, Yongshu,Zhang, Qiong,Tian, He,Zhu, Weihong,Nakatani, Keitaro
, p. 11685 - 11694,10 (2012/12/12)
Three photochromic compounds-2-butyl-5,6-bis[5-(4-methoxyphenyl)-2- methylthiophen-3-yl]-1 H-benzo[de]isoquinoline-1,3(2 H)-dione (BTE-NA), 4,5-bis[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]benzo[c][1,2,5]thiadiazole (BTA), and BTTA, which contain naphtha
Synthesis and physico-chemical properties in aqueous medium of all possible isomeric bromo analogues of benzo-1H-triazole, potential inhibitors of protein kinases
Wa?sik, Romualda,Wińska, Patrycja,Poznański, Jaros?aw,Shugar, David
experimental part, p. 7259 - 7268 (2012/08/28)
In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2α, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK a values for dissociation of the triazole proton. Experimental data (pKa, solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2α. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.
METHOD OF MANUFACTURING 3, 3' , 4, 4'-TETRAAMINOBIPHENYL
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Page/Page column 5, (2009/06/27)
An object of the present invention is to provide an efficient method of manufacturing 3,3′,4,4′-tetraaminobiphenyl with a smaller number of steps. The manufacturing method of 3,3′,4,4′-tetraaminobiphenyl includes reacting the amino groups of a 4-halo-o-phenylenediamine with an inorganic sulfur compound to lead to a 5-halo-2,1,3-benzothiadiazole, subsequently coupling two molecules of the benzothiadiazole together to form a 5,5′-bis(2,1,3-benzothiadiazole) and then deprotecting the amino groups to yield 3,3′,4,4′-tetraaminobiphenyl.
Pyridyl-substituted triazoles as tgf inhibitors
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, (2008/06/13)
Pyridyl substituted triazoles of formula (I) wherein R1 is naphthyl or phenyl optionally substituted with one or more substituents selected from the group consisting of halo, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, C1-6haloalkyl, —O—(CH2)n-Ph, —S—(CH2)n-Ph, cyano, phenyl, and CO2R, wherein R is hydrogen or C1-6alkyl, and n is 0, 1, 2 or 3; or R1 is phenyl fused with an aromatic or non-aromatic cyclic ring of 5-7 members wherein said cyclic ring optionally contains up to three heteroatoms, independently selected from N, O and S, and N may be further optionally substituted by C1-6 alkyl; R2 is H, C1-6alkyl, C1-6alkoxy, phenyl, NH(CH2)n-Ph, NH—C1-6alkyl, halo, CN, NO2, CONHR and SO2NHR; two of X1, X2 and X3 are N and the other is NR3 wherein R3 is hydrogen, C1-6alkyl, C3-7cycloalkyl, —(CH2)p—CN, —(CH2)p—CO2H, —(CH2)p—CONHR4R5, —(CH2)pCOR4, —(CH2)q(OR6)2, —(CH2)pOR4, —(CH2)q—CH═CH—CN, —(CH2)q—CH═CH—CO2H, —(CH2)p—CH═CH—CONHR4R5, (CH2)pNHCOR7 or (CH2)pNR8R9; R4 and R5 are independently hydrogen or C1-6alkyl; R6 is C1-6alkyl; R7 is C1-7alkyl, or optionally substituted aryl, heteroaryl, arylC1-6alkyl or heteroarylC1-6alkyl; R8 and R9 are independently selected from hydrogen, C1-6alkyl, aryl and arylC1-6alkyl; p is 04; and q is 1-4. and salts and solvates thereof, are disclosed, as are methods for their preparation, pharmaceutical compositions containing them and their use in medicine.
