132131-24-9Relevant articles and documents
Synthesis of 7-[123I]idotacrine: A potential SPECT agent to map acetylcholinesterase
Akula, Murthy R.,Kabalka, George W.
, p. 959 - 964 (1999)
9-Amino-1,2,3,4-tetrahydroacridine (Tacrine), a cognitive enhancer, is an inhibitor of the enzyme acetylcholinesterase. The synthesis of no-carrier-added 7-[123I]iodotacrine, was accomplished in four steps for potential use in mapping acetylcholinesterase.
Synthesis and in vitro biological evaluation of novel quinazoline derivatives
Zhang, Yaling,Zhang, Ying,Liu, Juan,Chen, Li,Zhao, Lijun,Li, Baolin,Wang, Wei
, p. 1584 - 1587 (2017)
A series of novel 4-arylamino-6-(5-substituted furan-2-yl)quinazoline derivatives were designed, synthesized and evaluated on biological activities in vitro. Compound 2a, 3a and 3c exhibited highly anti-proliferation activities on all tested tumor cell lines including SW480, A549, A431 and NCI-H1975 cells. Especially, compound 2a not only exhibited strong anti-proliferation activities against the tumor cell lines which expressed wild type or mutant EGFRL858R/T790M, but also showed the most potent inhibitory activity toward wild type EGFR (IC50?=?5.06?nM). The result of docking with EGFR suggested the binding mode of 2a was similar to that of lapatinib. While Western-blot analyses showed 2a obviously inhibited the activation of EGFR, Akt and Erk1/2 in lung cancer cells at indicated concentration. It is believed that this work would be very useful for developing a new series of TKIs targeting EGFR.
2-Cyano-4-iodo-acetanilide: A hydrogen-bonded chain of R 2 2(12) and R22(14) rings
Garden, Simon J.,Custodio, Cintia De A.,Wardell, James L.,Low, John N.,Glidewell, Christopher
, p. o408-o410 (2007)
The mol-ecules of 2-cyano-4-iodo-acetanilide, C9H7IN2O, are linked by N - H...N and C - H...O hydrogen bonds into chains of alternating R 2 2(12) and R 2 2(14) rings. International Union of Crystallography 2007.
A novel DMSO-assisted regioselective iodination of aniline analogues
Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye
, (2020/10/05)
A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.
Novel 4-arylaminoquinazolines bearing N,N-diethyl(aminoethyl)amino moiety with antitumour activity as EGFRwt-TK inhibitor
Zhang, Yaling,Chen, Li,Li, Xiabing,Gao, Li,Hao, Yunxia,Li, Baolin,Yan, Yaping
, p. 1668 - 1677 (2019/10/14)
Herein, four novel 4-arylaminoquinazoline derivatives with N,N-diethyl(aminoethyl)amino moiety were designed, synthesised and evaluated on biological activities in vitro. All synthesised compounds have inhibitory effects against tumour cells (SW480, A549, A431 and NCI-H1975). In particular, 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(5-((N,N-diethyl(aminoethyl))aminomethyl)furan-2-yl)quinazoline (6a) and 6-(5-((N,N-diethylethyl)aminomethyl)furan-2-yl)-4-(4-(E)-(propen-1-yl)phenylamino)quinazoline (6d) were potent antitumour agents which showed high antiproliferative activities against tumour cells in vitro. Moreover, compound 6a could induce late apoptosis of A549 cells at high concentrations and arrest cell cycle of A549 cells in the G0/G1 phase at tested concentrations. Also, compound 6a could inhibit the activity of wild type epidermal growth factor receptor tyrosine kinase (EGFRwt-TK) with IC50 value of 15.60 nM. Molecular docking showed that compound 6a formed three hydrogen bonds with EGFRwt-TK, while lapatinib formed only two hydrogen bonds with the receptor protein. It is believed that this work would be giving a reference for developing anti-cancer drugs targeted EGFR-TK.
Quinazoline-1-deoxynojirimycin hybrids as high active dual inhibitors of EGFR and α-glucosidase
Zhang, Yaling,Gao, Hongliang,Liu, Renjie,Liu, Juan,Chen, Li,Li, Xiabing,Zhao, Lijun,Wang, Wei,Li, Baolin
, p. 4309 - 4313 (2017/09/12)
A series of novel quinazoline-1-deoxynojirimycin hybrids were designed, synthesized and evaluated for their inhibitory activities against two drug target enzymes, epidermal growth factor receptor (EGFR) tyrosine kinase and α-glucosidase. Some synthesized compounds exhibited significantly inhibitory activities against the tested enzymes. Comparing with reference compounds gefitinib and lapatinib, compounds 7d, 8d, 9b and 9d showed higher inhibitory activities against EGFR (IC50: 1.79–10.71 nM). Meanwhile the inhibitory activities of 7d, 8d and 9c against α-glucosidase (IC50 = 0.14, 0.09 and 0.25 μM, respectively) were obvious higher than that of miglitol (IC50 = 2.43 μM), a clinical using α-glucosidase inhibitor. Interestingly, compound 9d as a dual inhibitor showed high inhibitory activity to EGFRwt tyrosine kinase (IC50 = 1.79 nM), also to α-glucosidase (IC50 = 0.39 μM). The work could be very useful starting point for developing a new series of enzyme inhibitors targeting EGFR and/or α-glucosidase.
Lapatinib intermediate and its preparation method and application
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Paragraph 0041-0043, (2016/10/09)
The invention discloses a lapatinib intermediate as well as a preparation method and application thereof. The lapatinib intermediate contains chemical structures respectively shown in a formula IV, a formula V and a formula VIII (described in the specification). The lapatinib intermediate provided by the invention has the advantages of simple preparation technology, available raw materials, mild reaction conditions, high yield, easy control on quality and the like; by applying the lapatinib intermediate, a preparation route of lapatinib can be shortened, operation is simple, reaction conditions are mild, especially adoption of poisonous reagents such as sulfoxide chloride and phosphorus oxychloride can be avoided, the lapatinib intermediate can be stable in each step, post treatment is simple, yield is high, the lapatinib intermediate is applicable to mass production and has practical value, and large-scale industrial production demand of lapatinib can be met.
NOVEL PROCESS FOR THE PREPARATION OF LAPATINIB AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
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Page/Page column 11, (2011/11/06)
The present invention relates to an improved and novel process for the preparation of high purity crystalline base of Lapatinib of formula-(1) having chemical name N-{3-chloro-4-[(3-fluorobenzyloxy]phenyl}-6-[5-({[2-(methanesulfonyl)ethyl]amino}methyl]-2-furyl]-4-quin-azolinamine and its pharmaceutically acceptable salts. The present invention further relates to intermediates according to formula (8) and formula (9) used in this process
NOVEL COMPOUNDS EFFECTIVE AS XANTHINE OXIDASE INHIBITORS, METHOD FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
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Page/Page column 46, (2011/04/26)
The present invention relates to novel compounds which are effective as an inhibitor for xanthine oxidase, a process for preparing the same, and a pharmaceutical composition comprising a therapeutically effective amount of the same.
A NEW PROCESS FOR THE PREPARATION OF LAPATINIB AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
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Page/Page column 13, (2011/04/25)
The present invention relates to an improved and new process for the preparation of high purity crystalline base of Lapatinib of formula (1) having chemical name N-{3-chloro-4-[(3-fluorobenzyloxy]phenyl}-6-[5-({[2-(methanesulfonyl) ethyl]amino}methyl]-2-furyl]-4-quin -azolinamine and its pharmaceutically acceptable salts.
