- Synthesis and Crystal Structures of Ethyl 2-(4-Methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate Dihydrate and Its Building Block 4-Fluoro-3-nitrobenzoic Acid
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The title compound, ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate (5), was synthesized and its crystal structure was studied by single-crystal X-ray diffraction technique. Compound 5 is crystallized in the centrosymmetric triclinic space group P1 ˉ with Z = 4 and Z′ = 2, and unit-cell parameters of a = 8.9190 (3) ?, b = 12.6888 (4) ?, c = 14.7111 (5) ?, α = 98.4855 (10)°, β = 101.6379 (9)°, γ = 95.4346 (10)° and V = 1599.43 (9) ?3. Its starting material, 4-fluoro-3-nitrobenzoic acid (1), is crystallized in the non-centrosymmetric monoclinic space group P21 and Z = 4 with unit-cell parameters of a = 3.7170 (4) ?, b = 12.6475 (13) ?, c = 15.5237 (15) ?, α = 90°, β = 91.9786 (16)°, γ = 90° and V = 729.35 (13) ?3. It was noted that strong hydrogen bonds play important roles in the crystal packing of both compounds, especially in 5, in which the co-crystallized water molecules act as both strong hydrogen bond donor and strong hydrogen bond acceptor. Graphical Abstract: Two molecule of compound 5 crystallized in a non symmetrical manner with four co-crystallized water molecules which play an important role in the crystal packing as strong hydrogen-bond donors. [Figure not available: see fulltext.].
- Yeong, Keng Yoon,Chia, Tze Shyang,Quah, Ching Kheng,Tan, Soo Choon
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p. 170 - 176
(2018/08/21)
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- ANTI-ANGIOGENIC AGENTS AND USES THEREOF
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There is herein disclosed a compound of formula I: or a salt solvate or pharmaceutically acceptable derivative thereof, wherein R1 to R7 is as defined herein for use in the treatment of angenogenis and related conditions.
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- COMPOUND AND METHOD FOR INHIBITING SIRTUIN ACTIVITIES
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A compound of formula wherein R1 is selected from the group consisting of hydrogen, halogen, hydroxyl, carboxyl, alkyl of up to 5 carbon atoms, imidazolyl, piperazinyl, morpholinyl, benzyl, R4OH or R4COOH, where R4 is (CH2)m and m is an integer of from 1 to 4; R2 is selected from the group consisting of hydrogen, phenyl or 3-(2-oxopyrrolidin-l-yl) propyl; and R3 is hydrogen or alkyl of from 1-4 carbon atoms.
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- Palladium(II)-catalyzed, heteroatom-directed, regioselective C-H nitration of anilines using pyrimidine as a removable directing group
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A new palladium-catalyzed, heteroatom-directed strategy for C-H nitration of anilines is described. This C-H functionalization reaction is highly ortho-selective and results in very good yields. The highlight of the work is the use of pyrimidine as the removable directing group. This approach constitutes one of the rare methods of ortho-nitration of anilines, a reaction that is normally very difficult to achieve via traditional approaches.
- Pawar, Govind Goroba,Brahmanandan, Abhilashamole,Kapur, Manmohan
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supporting information
p. 448 - 451
(2016/02/18)
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- As cell necrosis inhibitors of the indole compounds (by machine translation)
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The invention relates to chemical formula (1) indole compounds, or its pharmaceutically acceptable salt or isomer, and in containing the same as the characteristic, as an active ingredient for the prevention or treatment of cell necrosis and its associated disease composition and method of manufacturing. (by machine translation)
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Paragraph 0212; 0213
(2016/10/09)
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- INDOLE COMPOUND AS INHIBITOR OF NECROSIS
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The present invention relates to an indole compound represented by formula (1), a pharmaceutically acceptable salt or isomer thereof, a composition for prevention or treatment of necrosis and necrosis-associated diseases, and a method for preparing the composition, the composition comprising the indole compound or the pharmaceutically acceptable salt or isomer thereof as an active ingredient.
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Paragraph 0186
(2016/08/17)
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- Synthesis of 3,4-diaminobenzoyl derivatives as factor Xa inhibitors
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Abstract The coagulation factor Xa (FXa) plays a central role in the blood coagulation cascade. Recent studies have shown that FXa is a particularly attractive target for the development of oral antithrombotic agents. In view of the excellent pharmaceutical properties of 1,2-phenylenediamine-based FXa inhibitors and the reported structureeactivity relationship (SAR) analysis of FXa inhibitors, we designed and synthesized a series of 3,4-diaminobenzoyl-based FXa inhibitors. Intensive SAR studies on this new series led to the discovery of 3,4-dimethoxyl substituted compound 7b. 7b is a highly potent, selective, direct FXa inhibitor with excellent in vivo antithrombotic activity.
- Yang, Jiabin,Su, Guoqiang,Ren, Yu,Chen, Yang
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- Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
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Abstract A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as 1H NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain using BacTiter-Glo Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with IC50 of less than 15 μM. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 μM.
- Yoon, Yeong Keng,Ali, Mohamed Ashraf,Wei, Ang Chee,Choon, Tan Soo,Ismail, Rusli
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p. 614 - 624
(2015/03/18)
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- Discovery of a potent and highly fluorescent sirtuin inhibitor
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In search for potent sirtuin inhibitors, a series of diversified 1,2-disubstituted benzimidazole analogues were synthesized using a one-pot method. The most potent compound in the series (BZD9L1) was discovered to show high autofluorescence which can be utilized to predict its localization in cells. More importantly, BZD9L1 displayed strong antiproliferative effects against a panel of cancer cells tested. Molecular docking studies also help to explain the observed structure-activity relationship.
- Yoon,Ali,Wei,Choon,Shirazi,Parang
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p. 1857 - 1863
(2015/10/20)
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- Indole and indazole compounds as an inhibitor of cellular necrosis
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The present invention refers to a formula (1) compounds of, pharmaceutically acceptable salts or isomers thereof thereof, and characterized by by containing as active ingredients-associated diseases, cell death and method for the prevention or treatment of relates and compositions. [Formula 1] In formula said R 1, R 2, R 3, R 4, R 5, R 6, A, X, n and m to equal the specification.
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Paragraph 0339; 0344-0346; 0349
(2016/10/08)
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- Chromoionophore and method of determining potassium ions
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The invention relates to methods of determining potassium ions in a sample, wherein the ions are contacted with a compound having chromophoric moiety and an ionophoric moiety, where the ionophoric moiety interacts with the potassium ions present in the sample, resulting in the chromophoric moiety changing its radiation absorption properties in the ultraviolet and visible regions of the spectrum. For example, a change in an intensity of an absorption maximum is measured and the ion concentration is determined accordingly.
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Page/Page column 16-17
(2011/06/25)
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- NOVEL PROTEIN KINASE MODULATORS
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The invention provides compounds that inhibit selected kinases (Pirn, Fit and/or CK2 kinases) and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, and certain infections and immunological disorders.
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Page/Page column 64
(2010/12/18)
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- INDOLE AND INDAZOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
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The present invention relates to indole or indazole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole or indazole compounds as an active ingredient.
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Page/Page column 12
(2010/08/08)
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- INDOLE AND INDAZOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
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The present invention relates to indole or indazole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole or indazole compounds as an active ingredient.
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Page/Page column 43
(2009/04/25)
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- Novel bicyclic sulfonamide derivatives which are L-CPT1 inhibitors
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The invention is concerned with novel heterobicyclic derivatives of formula (I) wherein R1, R2, R3, R4, R5, R6, V, W, X and Y are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit L-CPT1 and can be used as medicaments.
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Page/Page column 27
(2010/11/28)
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- HYDROXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE
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The present invention relates to novel hydroxyethylamine compounds of formula (I): (I) having Asp2 (-secretase, BACE1 or Memapsin) inhibitory activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by elevated-amyloid levels or-amyloid deposits, particularly Alzheimer's disease.
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- REMEDIES FOR POLYCYSTIC OVARY SYNDROME
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The present invention relates to a therapeutic agent for polycystic ovary syndrome, which comprises a compound of the following formula (1) or (2), or a pharmaceutically acceptable salt thereof as an active ingredient: wherein each symbol is as defined in the specification.
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- Aromatic amino ethers as pain relieving agents
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The present invention relates to compounds of formula (I), STR1 wherein A is an optionally substituted phenyl naphthyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidyl, thienyl, thiazolyl, oxazolyl, thiadiazolyl having at least two adjacent ring carbon atoms or a bicyclic ring system, provided that the --CH(R3)N(R2)B--R1 and --OCH(R4 --)--D linking groups arm positioned in a 1,2 relationship to one another on ring carbon atoms and the ring atom positioned ortho to the --OCHR4 -- linking group (and therefore in the 3-position relative to the --CHR3 NR2 -- linking group) is not substituted; B is an optionally substituted ring system; D is an optionally substituted ring system; R1 is a variety of group as defined in the description; R2 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, phenylC1-3 alkyl or 5- or 6-membered heteroarylC1-3 alkyl; R3 is hydrogen or C1-4 alkyl; R4 is hydrogen or C1-4 alkyl; and N-oxides of NR2 where chemically possible; and S-oxides of sulphur containing rings were chemically possible; and pharmaceutically acceptable salts and in vivo hydrolysable esters and amides thereof. Process for their preparation, intermediates in theirpreparation, their use as therapeutic agents and pharmaceutical compositions containing them.
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- Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides
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Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.
- Monge, Antonio,Palop, Juan A.,Cerain, Adela Lopez de,Senador, Virginia,Martinez-Crespo, Francisko J.,et al.
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p. 1786 - 1792
(2007/10/02)
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- Studies in Antiparasitic Agents: Part 9 - Synthesis of 5(6)-Alkoxycarbonyl-2-substituted-benzimidazoles as Potential Anthelmintics
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Methyl 5(6)-alkoxycarbonylbenzimidazole-2-carbamates (5a-5f) and 5(6)-carboxyl analogue (5g) and its salts (6a-6b) have been synthesized starting from 4-amino-3-nitrobenzoic acid (2), and their structures established by elemental analysis and spectral data.The drugs 5a-5g and 6a-6b have been tested for their anthelmintic activity in rodents infested by Ancylostoma ceylanicum, Syphacia obvelata, Nippostrongylus brasiliensis, Hymenolepis nana, Cysticercus fasciolaris, Litomosoides carinii and Dipetalonema viteae and found to cause 100percent elimination of A. ceylanicum hookworms at an oral dose of 25-250 mg/kg but not so effective against other helminths.
- Naim, S. Shawkat,Singh, Sudhir K.,Sharma, Satyavan,Gupta, Suman,Fatma, N.,et al.
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p. 1106 - 1109
(2007/10/02)
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