36185-83-8Relevant articles and documents
Synthesis, characterization, crystal structure, Hirshfeld interaction and bio-evaluation studies of 4-amino quinazoline sulfonamide derivatives
Sunil Kumar,Kudva, Jyothi,Madan Kumar,Vishwanatha,Kumar, Vasantha,Naral, Damodara
, p. 142 - 153 (2018)
In the present work, two new potentially active quinazolin-4-yl-aminobenzenesulfonamide derivatives, N-(5-methyl-1,2-oxazol-3-yl)-4-[(quinazolin-4-yl)amino]benzene-1-sulfonamide (4a) and N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-[(quinazolin-4-yl)amino]benzene-1-sulfonamide (4b), were synthesized and the structures were confirmed by different spectroscopic techniques like FT-IR, 1H NMR, 13C NMR, HRMS and elemental analysis. The crystal structures were solved by single crystal X-ray diffraction (XRD) studies. The single crystal XRD studies revealed that the compound 4a crystallized in monoclinic crystal system in P 21/n space group with Z = 4 and compound 4b crystallized in triclinic crystal system in P-1 space group with Z = 2. The XRD study has explained the intramolecular interactions of the title compounds. The thermal behaviour was determined with the aid of differential scanning calorimetry (DSC) and thermogravimetry-differential thermal analysis (TG-DTA). Further, the Hirshfeld surface analysis with finger plots and the electrostatic potential map has shown the nature of interactions and percentage contribution from each individual intermolecular contact of these title compounds. The H?H interactions have maximum contributions and C?H, O?H and N?H also have shown major contributions to the total area of the surface. In vitro antimicrobial activity studies have disclosed that the compound 4b exhibited a moderate antibacterial activity against B. Subtilis and E. Coli strains and excellent activity against the fungal strain, A. Niger. In vitro anticancer activity of the compounds 4a and 4b was also screened against MCF 7 and MDA-MB-231 breast cancer cell lines and revealed that there is no significant effect of substitution on biological activity for the synthesized compounds.
Naphthalimide-polyamine conjugate as well as preparation method and application thereof
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Paragraph 0030; 0108-0111, (2021/02/10)
The invention discloses a naphthalimide-polyamine conjugate, which has a structural general formula as shown in I, a novel skeleton, high efficiency, low toxicity and good inhibitory activity for tumor cells. The invention also discloses a preparation method of the conjugate. Firstly, 3-amino groups with toxic and side effects of amonafide are removed, a phenylpyrazole structure fragment is introduced to the naphthalimide parent naphthalene ring, and a naphthalimide side chain with a polyamine chain is modified, acetyltransferase in vivo is prevented from acetylating the amino groups on the naphthalene ring of amonafideand, and toxic and side effects are reduced; and further by introducing a low-toxicity phenyl pyrazole active structure fragment, the naphthalimide polyamine conjugate witha novel skeleton, high efficiency and low toxicity is synthesized; and secondly, quinazoline with low toxicity is introduced to replace hydrogen atoms of amonafide 3-amino, so that the naphthalimide polyamine conjugate with anti-tumor activity and low toxicity is obtained. The invention also discloses an application of the conjugate in preparation of antitumor drugs, and good development potentialis realized.
Catalyst and solvent switched divergent C-H functionalization: Oxidative annulation of: N -aryl substituted quinazolin-4-amine with alkynes
Meesa, Siddi Ramulu,Naikawadi, Praveen Kumar,Gugulothu, Kishan,Shiva Kumar
supporting information, p. 3032 - 3037 (2020/05/08)
The development of site-selective C-H functionalizations/annulations is one of the most challenging practices in synthetic organic chemistry particularly for substrates bearing several similarly reactive C-H bonds. Herein, we describe catalyst and solvent controlled ortho/peri site-selective oxidative annulation of C-H bonds of N-aryl substituted quinazolin-4-amines with internal alkynes. The ortho C-H selective annulation was observed using Pd-catalyst in DMF to give indole-quinazoline derivatives, while, Ru-catalyst in PEG-400 favoured the peri C-H bond annulation exclusively to furnish pyrido-quinazoline derivatives.
Design, synthesis and evaluation of novel hybrids between 4-anilinoquinazolines and substituted triazoles as potent cytotoxic agents
Le-Nhat-Thuy, Giang,Dinh, Thuy Van,Pham-The, Hai,Nguyen Quang, Hung,Nguyen Thi, Nga,Dang Thi, Tuyet Anh,Hoang Thi, Phuong,Le Thi, Tu Anh,Nguyen, Ha Thanh,Nguyen Thanh, Phuong,Le Duc, Trung,Nguyen, Tuyen Van
, p. 3741 - 3747 (2018/10/20)
In this research several series of novel dioxygenated ring fused 4-anilinoquinazolines (10a-d) and 4-anilinoquinazoline-substituted triazole hybrid compounds (11–14) have been designed and synthesized. Their biological significance was highlighted by evaluating in vitro for anticancer activities, wherein several compounds displayed excellent activity specifically against three human cancer cell lines (KB, epidermoid carcinoma; HepG2, hepatoma carcinoma; SK-Lu-1, non-small lung cancer). Especially, compound 13a exhibited up to 100-fold higher cytotoxicity in comparison with erlotinib. Docking the most cytotoxic compounds (11d, 13a, 13b, and 14c) into the ATP binding site of different EGFR tyrosine kinase domains was perfomed to predict the analogous binding mode of these compounds to the EGFR targets.
Novel compound or pharmaceutically acceptable salt thereof and pharmaceutical composition for prevention or treatment of disease caused by influenza virus infection containing the same as an active ingredient
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Paragraph 0680; 0681; 0682, (2016/10/08)
The present invention relates to a novel compound or pharmaceutically acceptable salt thereof, and to a pharmaceutical composition containing the same as an active ingredient for treating and preventing disease caused by influenza virus infection. The novel compound represented by chemical formula 1 according to the present invention not only has extremely excellent antivirus activity, but also has less side effects for a human body by not having cytotoxicity for a human cell. Therefore, a pharmaceutical composition containing the same as an active ingredient can be used in preventing or treating such as flu, colds, sore throats, bronchitis, pneumonia, bird flu, swine flu, and goat flu caused by influenza virus infection.COPYRIGHT KIPO 2015
A novel strategy to the synthesis of 4-anilinoquinazoline derivatives
Wang, Zheng,Wang, Cuiling,Sun, Yanni,Zhang, Ning,Liu, Zhulan,Liu, Jianli
, p. 906 - 913 (2014/01/23)
A novel approach to prepare 4-anilinoquinazoline derivatives based on the transformation of indoline-2,3-dione to formamidine was developed. The processes with this approach are simple, efficient, and environmentally friendly. The efficiency of this approach was evaluated by synthesizing 17 4-anilinoquinazolines and comparing the obtained yields with those achievable through conventional synthetic methods. It was the first time that compounds 8d, 8e, 8h, and 13b-f were synthesized. The characteristics of the IR and the UV spectra of these compounds and the effects of their substituents on the spectra were observed.
Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent
Foucourt, Alicia,Dubouilh-Benard, Carole,Chosson, Elizabeth,Corbière, Cécile,Buquet, Catherine,Iannelli, Mauro,Leblond, Bertrand,Marsais, Francis,Besson, Thierry
experimental part, p. 4495 - 4502 (2010/07/08)
A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to Azixa (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits.
