401485-19-6Relevant articles and documents
Pi-conjugated chain extenders for the synthesis of optoelectronic segmented polyurethanes
Harvey, Christopher P.,Tovar, John D.
, p. 4861 - 4874 (2011)
The optical properties of mechanochromic materials change under mechanical stress. Segmented polyurethanes are elastomers composed of amorphous, saturated chain soft segments, and rigid pi-conjugated hard domains. Within aggregates of hard domains pi-pi interactions may form and result in perturbation of the optoelectronic properties of the system. Disruption and restoration of these electronic interactions within the material may lead to observable mechanochromic response. A series of oligothiophene diols and diamines, as well as a naphthalene diimide diol, have been synthesized for incorporation into the hard domains of segmented polyurethanes and polyureas using long poly(tetramethylene oxide) chains as soft segments. The resulting polymers were evaluated to determine their extent of polymerization and their thermal stability. The optical properties of the materials were studied in solution and as thin films. Where possible the electrochemical properties of the polymers were also explored. The length of the soft segment chains in the segmented polyurethanes hindered electronic coupling of hard domains. Future work involving smaller, more solubilizing soft segments may allow for easier material characterization and mechanochromic response.
Identification of Pyrazolo[1,5- a]pyridine-3-carboxamide Diaryl Derivatives as Drug Resistant Antituberculosis Agents
Hu, Xianglong,Wan, Baojie,Liu, Yang,Shen, Jiayi,Franzblau, Scott G.,Zhang, Tianyu,Ding, Ke,Lu, Xiaoyun
, p. 295 - 299 (2019)
A series of pyrazolo[1,5-a]pyridine-3-carboxamide (PPA) derivatives bearing diaryl side chain was designed and synthesized as new antituberculosis agents, aiming to improve the efficacy toward drug resistant Mycobacterium tuberculosis (Mtb) strains. Most
Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines
Ingale, Ajit P.,Garad, Dnyaneshwar N.,Ukale, Dattatraya,Thorat, Nitin M.,Shinde, Sandeep V.
supporting information, p. 3791 - 3804 (2021/11/04)
Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.
Tuning the sensitivity towards mercury: Via cooperative binding to d-fructose: Dual fluorescent chemosensor based on 1,8-naphthyridine-boronic acid derivative
Rajadurai, Marina,Reddy, E. Ramanjaneya
, p. 14862 - 14870 (2021/05/19)
A novel fluorescent chemosensor naphthyridine-boronic acid derivative (1.1) was synthesized and its ability to act as a selective chemosensor was examined for various metal ions. Compound 1.1 displayed highly selective fluorescence quenching upon interaction with Hg2+, possibly by means of photo induced electron transfer (PET) mechanism. The binding stoichiometry of the naphthyridine-boronic acid-Hg2+ complex and the association constant was determined. It was found that in the presence of d-fructose at physiological concentration, the sensitivity of chemosensor 1.1 towards Hg2+ improved by at least 7 times, perhaps as a result of the cooperative binding of both d-fructose and mercury ion to the sensor. Till now, the presented dual d-fructose-mercury chemosensor is the first example of utilizing boronic acid-diol complexation for enhancement of the sensor's sensitivity towards a toxic metal ion. The utility of compound 1.1 lays in applications in the food industry, e.g. for detection of mercury contamination of high fructose corn syrup, or in estimation of mercury in polluted biological samples and underground water. This journal is
Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst
Awasthi, Amardeep,Mukherjee, Anagh,Singh, Mandeep,Rathee, Garima,Vanka, Kumar,Chandra, Ramesh
, (2020/05/14)
An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.
Novel quinazoline EGFR inhibitor, and preparation method and application thereof
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Paragraph 0026, (2019/10/01)
A novel quinazoline EGFR inhibitor, and a preparation and an application thereof belong to the field of synthesis of medicines. The novel quinazoline EGFR inhibitor has a general formula shown in thedescription; and in the general formula, R is one from H, F, Cl, Br, and I, and R1 and R2 are same to or different from each other, and are respectively selected from H, a nitro group, an amino group,a hydroxyl group, a 2-methoxyethoxy group, a C1-C4 alkoxy group and a C1-C4 alkyl group. The novel quinazoline EGFR inhibitor is different from existing quinazoline inhibitors with the 4-position substituted with various anilines, and is designed and synthesized by substituting the 4-position of a quinazoline skeleton with a broadly bioactive thienylmethylamine and reasonably modifying the 6-position and the 7-position with groups not including an electrophilic acrylamide bond in order to avoid covalent bonds with EGFR. Compared with existing antitumor drugs, the above compound can significantly inhibit EGFR phosphorylation, and has excellent anti-proliferative activity against EGFR overexpressing tumor cells (such as A431 and MCF-7).
COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN
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Paragraph 0040; 0059, (2020/09/17)
Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting of N6-[(3-halothien-2-yl)methyl]adenosine, N6-[(4-halothien-2-yl)methyl]adenosine, and N6-[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting of N6-[(2-bromothien-3-yl)methyl]adenosine, N6-[(4-bromothien-3-yl)methyl]adenosine, N6-[(5-bromothien-3-yl)methyl]adenosine N6-[(2-chlorothien-3-yl)methyl]adenosine, N6-[(4-chlorothien-3-yl)methyl]adenosine, and N6-[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.
Synthesis and biological evaluation of some novel thiophene-bearing quinazoline derivatives as EGFR inhibitors
Zou, Min,Jin, Bo,Liu, Yanrong,Chen, Huiping,Zhang, Zhuangli,Zhang, Changzheng,Zhao, Zhihong,Zheng, Liyun
, p. 102 - 110 (2019/01/04)
Background: With the approval of gefitinib, erlotinib, afatinib, and osimertinib for clinical use, targeting Epidermal Growth Factor Receptor (EGFR) has been intensively pursued. Similar to most therapies, challenges related to the treatment resistance against these drugs have emerged over time, so new EGFR Tyrosine Kinase Inhibitors (TKIs) need to be developed. This study aimed to investigate the potential use of a series of thiophene-bearing quinazoline derivatives as EGFR inhibitors. We designed and synthesized nine quinazolin derivatives, among which five compounds (5e, 5f, 5g, 5h, and 5i) were reported for the first time. Methods: Two cancer cell lines, A431 (overexpressing EGFR) and A549 (EGFR wild-type and K-ras mutation), were treated by these compounds and subjected to MTT assay. The A431 cells were selected for further treatment (5e) and Western blot analysis. Results: Although the compounds exerted no obvious effects on the proliferation of A549 cells, seven out of the nine compounds significantly inhibited the growth of A431 cells. In particular, the IC50 values of 5e and erlotinib were nearly equal. Western blot results showed that 5e significantly inhibited EGFR autophosphorylation in A431 cells. Structure-activity relationships indicated that quinazolines bearing 6,7-side chains were more potent than those unsubstituted at the 6,7-positions. Moreover, electron-withdrawing hydrophobic groups on the 5-position of the thiophene were preferred, such as chlorine or bromine atom. Conclusion: Nine 4-aminoquinazolin derivatives were designed, synthesized, and evaluated against A431 and A549 cell lines. Seven compounds significantly inhibited the growth of A431 cells. In particular, 5e possessed similar antitumor potency to that of erlotinib.
COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN
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Paragraph 0040; 0059, (2019/01/06)
Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting ofN 6 -[(3-halothien-2-yl)methyl]adenosine,N 6 -[(4-halothien-2-yl)methyl]adenosine, andN 6 -[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting ofN 6 -[(2-bromothien-3-yl)methyl]adenosine,N 6 -[(4-bromothien-3-yl)methyl]adenosine,N 6 -[(5-bromothien-3-yl)methyl]adenosineN 6 -[(2-chlorothien-3-yl)methyl]adenosine,N 6 -[(4-chlorothien-3-yl)methyl]adenosine, andN 6 -[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.
Pyrazolo[1, 5-a]pyridine compound and use thereof
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Paragraph 0363; 0364; 0365; 0366; 0367, (2016/10/08)
The invention discloses a pyrazolo[1, 5-a]pyridine compound with the structure characteristic shown in the formula (I) or its pharmaceutically acceptable salt, stereoisomer or prodrug molecule and a use thereof. The compound has good in-vitro anti-tubercle bacillus activity, has the minimal inhibitory concentration (MIC) less than 0.1 micrograms per milliliter and partial MIC of 0.01 micrograms per milliliter and has strong inhibition effects on a clinically sorted multi-drug-resistant tuberculosis (MDR-TB) strain. In an in-vivo experiment, at a dosage of 20mg/kg/d, the pyrazolo[1, 5-a]pyridine compound can effectively eliminate H37Ra infection in a mouse and is a novel anti-tuberculosis compound.
