- Structural revision of the Mcl-1 inhibitor MIM1: synthesis and biological studies on ovarian cancer cells with evaluation of designed analogues
-
In the area of cancer research, the development of new and potent inhibitors of anti-apoptotic proteins is a very active and promising topic. The small molecule MIM1 has been reported earlier as one of the first selective inhibitors of the anti-apoptotic protein Mcl-1. In the present paper, we first revised the structure of this molecule based on extensive physicochemical analyses. Then we designed and synthesized a focused library of analogues for the corrected structure of MIM1. Next, these molecules were subjected to a panel ofin cellulobiological studies, allowing the identification of dual Bcl-xL/Mcl-1 inhibitors, as well as selective Mcl-1 inhibitors. These results have been complemented by fluorescence polarization assays with the Mcl-1 protein. Preliminary structure-activity relationships were discussed and extensive molecular modelling studies allowed us to propose a rationale for the biological activity of this series of new inhibitors, in particular for the selectivity of inhibition of Mcl-1versusBcl-xL
- Bignon, Jér?me,Brotin, Emilie,Denoyelle, Christophe,El Dine, Assaad Nasr,Elie, Nicolas,Grée, René,Hachem, Ali,Hedir, Siham,Jouanne, Marie,Justaud, Frédéric,Levoin, Nicolas,Paysant, Hippolyte,Poulain, Laurent,Roisnel, Thierry,Roussi, Fanny,Soulieman, Ali,Tasseau, Olivier,Voisin-Chiret, Anne Sophie,Weiswald, Louis Bastien
-
p. 8968 - 8987
(2021/11/04)
-
- A thiosemicarbazone–palladium(II)–imidazole complex as an efficient pre-catalyst for Suzuki–Miyaura cross-coupling reactions at room temperature in aqueous media
-
Abstract: A Pd(II) complex of two sterically crowded ligands, specifically an N,S-donor thiosemicarbazone and an N-donor imidazole, has been synthesized and characterized by physicochemical and spectroscopic methods. X-ray single-crystal analysis revealed that the coordination geometry around the palladium center is distorted square planar, and the chloride ligand is involved in intermolecular bifurcated X–HY-type (where X?=?C, N and Y?=?Cl) hydrogen bonding. This complex proved to be a highly active and retrievable pre-catalyst for additive-free Suzuki–Miyaura cross-coupling reactions of arylboronic acids with aryl bromides or chlorides at room temperature and 60?°C, respectively. The reactions require a low catalyst loading and the complex is converted to ~1.5–2.0 nm-sized Pd nanoparticles (probably the real catalyst). The catalyst can be reused up to seven times without significant loss in activity. Since the reaction proceeds under mild conditions in aqueous medium and the catalyst is recoverable, it provides an environmentally benign alternative to the existing protocols for Suzuki–Miyaura reactions. Graphical abstract: Biaryls can be synthesized in high yield under greener reaction conditions in the presence of efficient pre-catalyst, thiosemicarbazone–palladium(II)–imidazole.[Figure not available: see fulltext.].
- Baruah, Jayantajit,Gogoi, Rajjyoti,Gogoi, Nibedita,Borah, Geetika
-
p. 683 - 692
(2017/09/06)
-
- Carbothioamide as Highly Efficient Ligand for Copper-catalyzed Room Temperature Chan–Lam Cross-Coupling Reaction
-
The catalytic activity of three N,S-donor ligands, viz L1 [2-(4-methoxybenzylidene)-N-phenylhydrazinecarbothioamide], L2 [2,2′-(1,2-diphenylethane-1,2-diylidene)bis(hydrazinecarbothioamide)] and L3 [2-(4-methoxybenzylidene)hydrazinecarbothioamide] has been reported for N-arylation of imidazoles with arylboronic acids in ethanol at room temperature. The method was found to be applicable in N-arylation for a wide range of electronically diverse arylboronic acids with imidazoles having modest to excellent isolated yields. The in situ generated copper(II) complex of the ligand namely, 2-(4-methoxybenzylidene)-N-phenylhydrazinecarbothioamide (L1) was found to be highly efficient homogeneous catalyst for N-arylation reaction.
- Baruah, Jayantajit,Gogoi, Kongkona,Dewan, Anindita,Borah, Geetika,Bora, Utpal
-
supporting information
p. 1203 - 1208
(2017/10/25)
-
- One-pot two-step facile synthesis of 2,3,4,5-tetra substituted dihydrooxazoles and their antimicrobial activity
-
New 2,3,4,5-tetra substituted dihydrooxazoles derivatives were efficiently synthesized starting from benzaldehyde, aryl thiosemicarbazide and benzoin using designed synthetic route. Newly synthesized 2,3,4,5-tetra substituted dihydrooxazole derivatives we
- Tiwari, Shailendra,Pathak, Poonam,Pratap Singh, Kamal,Sagar, Ram
-
supporting information
p. 3802 - 3805
(2017/07/27)
-
- Efficient synthesis of novel 2,3-dihydro-1,3,5,4-thiadiazaphosphole derivatives
-
ABSTRACT: The condensation of various thiosemicarbazones with methyl thiophene-2-carboximidate afforded the corresponding intermediates 2a–2h. Subsequent cyclization of the latter compounds with hexamethylphosphorous triamide constitutes a new route to the synthesis of novel highly functionalized thiadiazaphosphole derivatives 4a–4h. This method offers significant advantages such as efficiency, high yields and mild reaction conditions.
- Balti, Monaem,Efrit, Mohamed Lotfi
-
p. 466 - 475
(2016/07/23)
-
- Ni(II), Cu(II) and Pd(II) complexes of anisaldehyde-4-phenyl-thiosemicarbazone: Synthesis, spectral characterization and biological study
-
Anisaldehyde-4-phenyl-thiosemicarbazone (HL) complexes of Ni(II), Cu(II) and Pd(II) have been synthesized. Conductivity measurements, spectroscopic (FTIR, UV-visible, ESI(+) mass, 13C and 1H NMR, ESR), cyclic voltammetry study and th
- Baruah, Jayantajit,Borah, Geetika,Kardong, Devid
-
p. 2446 - 2452
(2016/10/19)
-
- Synthesis and antimicrobial studies of novel 2,4-diaryl-3-azabicyclo[3.3.1] nonan-9-one 4′-phenylthiosemicarbazones
-
New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one 4′-phenylthiosemicarbazones (compounds 9-16) was obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones. The synthesized compounds have been characterized by their elemental, anal
- Umamatheswari, Seeman,Kabilan, Senthamaraikannan
-
p. 430 - 439
(2012/01/06)
-
- Inhibition of xanthine oxidase by thiosemicarbazones, hydrazones and dithiocarbazates derived from hydroxy-substituted benzaldehydes
-
Nonpurine xanthine oxidoreductase (XOR) inhibitors represent important alternatives to the purine analogue allopurinol, which is still the most widely used drug in the treatment of conditions associated with elevated uric acid levels in the blood. By cond
- Leigh, Maria,Raines, Daniel J.,Castillo, Carmen E.,Duhme-Klair, Anne K.
-
experimental part
p. 1107 - 1118
(2012/01/03)
-
- Synthesis, structures, and property studies on Zn(II), Ni(II), and Cu(II) complexes with a Schiff base ligand containing thiocarbamide group
-
A Schiff base ligand containing thiocarbamide group of 4-phenyl-1-(4-methoxyl-1-phenylethylidene)thiosemicarbazide (HL) and its three mononuclear metal complexes of ZnL2 (1), NiL2 (2), and CuL2 (3) have been synthesized. E
- Zhao, Pu Su,Wang, Hong Yan,Song, Jie,Lu, Lu De
-
experimental part
p. 977 - 987
(2011/11/05)
-
- One-pot and catalyst-free synthesis of thiosemicarbazones via multicomponent coupling reactions
-
A novel and efficient procedure for the synthesis of thiosemicarbazones has been achieved via a multicomponent and catalyst-free reaction of phenyl or p-chlorophenyl isothiocyanate, hydrazine, and aldehydes or ketones. The method afforded 20 thiosemicarba
- Cunha, Silvio,Silva, Tiago Lima da
-
experimental part
p. 2090 - 2093
(2009/09/05)
-
- On the synthesis of fused thiazolo[5,4-d]isoxazoles and a novel rearrangement involving conversion of 5(4H)-isoxazolones to 4(5H)-isoxazolones
-
The interaction of 4-bromo-3-substituted-(4H)-isoxazol-5-ones (1) with alkyl/aryl thiocarbamides (2), 4-alkyl/aryl thiosemicarbazides (7) and 2, 4-disubstituted thiosemicarbazides (12) afford 5-alkyl/ arylamino-3-substituted-thiazolo [5, 4-d]isoxazoles (3) and 6-amino/anilino-5-alkyl/arylimino-3-substituted-thiazolo[5, 4-d]isoxazoles respectively. An alternate unambiguous one step synthesis is described. The compounds have been characterised by chemical reactions and spectral data.
- Chande,Joshi
-
p. 403 - 409
(2007/10/03)
-
- Novel synthesis of new 5,7-disubstituted-2-alkyl/arylamino-4H-pyrazolothiadiazines and 4,6-disubstituted-3-amino/anilino-2-alkyl/aryliminopyrazolothiazolines
-
The title compounds have been prepared by the interaction of substituted 4-bromopyrazolin-5-ones with thiosemicarbazides.An alternate unambiguous synthesis of pyrazolothiazolines has been described.All the compounds have been characterised by spect
- Chande, Madhukar S.,Joshi, Rajesh D.
-
p. 289 - 301
(2007/10/02)
-
- On the Reaction of Derivatives of Thiosemicarbazide with Bis-Imidochlorides of Oxalic Acid
-
Arylsubstituted oxalic bis-imidochlorides 1 react with thiosemicarbazones of type 5 as well as 13 to give five-membered-ring heterocycles 8, 11, and 16. 13C-NMR spectroscopy, chemical methods and X-ray crystallography have been used to investigate the nature of the structures obtained.The 13C-chemical shifts of 13 and imidazolidines 16 are correlated with Hammett ?p constants and dual substituent parameters to evaluate the transmission of the X substituent electronic effects via the side-chain iminyl carbon atom into the heterocyclic ring and its neighbouring phenyl groups. - Keywords. 13C-NMR, Derivatives of oxalic acid; DSP-Analysis; NS-Heterocycles; Thiosemicarbazones; X-Ray crystallography.
- Beckert, Rainer,Gruner, Margit,Seidel, Ingeborg,Kuban, Ralf-Juergen
-
p. 1125 - 1138
(2007/10/02)
-
- Studies of Bivalent Metal Complexes of p-Chloro- and p-Methoxy-benzylidene-4-phenylthiosemicarbazone
-
Bivalent metal complexes of p-chloro- and p-methoxy-benzylidene-4-phenylthiosemicarbazones (H2CBPT and H2MBPT = H2L) have been prepared.The complexes prepared are of the types M(HL)2*nH2O (M = Co, Ni or Zn, n = 0-2), M(HL)X*nH2O (M = Cu or Hg; X = Cl or A
- El-Asmy, A. A.,Morsy, M. A.,El-Shafei, A. A.
-
p. 766 - 769
(2007/10/02)
-