- Synthesis and properties of alkyl chain substituted naphthalenetetracarboxylic monoanhydride monoimides and unsymmetrically substituted naphthalene derivatives
-
1,4,5,8-Naphthalenedianhydride is converted to N-(2-ethylhexyl)-1,4,5,8-naphthalenetetracarboxylic monoanhydride monoimide (2a) and N-(2-hydroxyethyl)-1,4,5,8-naphthalenetetracarboxylic monoanhydride monoimide (2c) through the potassium salt prepared from
- Koz, Banu,Demic, Serafettin,Icli, Siddik
-
-
Read Online
- The First Synthesis of Protected 5-Hydroxymethyl-2-cyanomethylbenzimidazole
-
Protected 5-hydroxymethyl-2-cyanomethylbenzimidazole 4 has successfully been synthesized starting from 3,4-diaminobenzoic acid 1. The benzimidazole 4 is expected to be a useful intermediate for the synthesis of new functional molecules such as drugs, agro
- Katsuyama, Isamu,Kubo, Masanori
-
-
Read Online
- Amide and ester derivatives of chlorido[4-carboxy-1,2-disalicylideneaminobenzene]iron(iii) as necroptosis and ferroptosis inducers
-
In continuation of the structure-activity study about 4-substituted chlorido[N,N'-disalicylidene-1,2-phenylenediamine]iron(iii) complexes as necroptosis and ferroptosis inducers, we introduced a 4-COOH group at the 1,2-phenylenediamine moiety of the lead
- Baecker, Daniel,Gust, Ronald,H?rschl?ger, Carina,Kircher, Brigitte,Ma, Benjamin N.,Sagasser, Jessica,Schultz, Lukas,Steiner, Lucy,Weinreich, Maria
-
supporting information
p. 6842 - 6853
(2020/06/08)
-
- 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
-
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
-
p. 170 - 176
(2018/08/21)
-
- BENZOIMIDAZOLE DERIVATIVES AS ANTICANCER AGENTS
-
The invention relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing said compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading t
- -
-
Page/Page column 39
(2018/04/20)
-
- COMPOUND AND METHOD FOR INHIBITING SIRTUIN ACTIVITIES
-
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.
- -
-
Page/Page column 9; 10
(2017/01/26)
-
- ANTI-ANGIOGENIC AGENTS AND USES THEREOF
-
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.
- -
-
Page/Page column 16
(2017/04/11)
-
- Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
-
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
-
p. 614 - 624
(2015/03/18)
-
- Discovery of a potent and highly fluorescent sirtuin inhibitor
-
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
-
p. 1857 - 1863
(2015/10/20)
-
- DNA intercalating RuII polypyridyl complexes as effective photosensitizers in photodynamic therapy
-
Six substitutionally inert [RuII(bipy)2dppz]2+ derivatives (bipy=2,2′-bipyridine, dppz = dipyrido[3,2-a:2′,3′-c]phenazine) bearing different functional groups on the dppz ligand [NH2 (1),OMe (2),OAc (3),OH (4),C
- Mari, Cristina,Pierroz, Vanessa,Rubbiani, Riccardo,Patra, Malay,Hess, Jeannine,Spingler, Bernhard,Oehninger, Luciano,Schur, Julia,Ott, Ingo,Salassa, Luca,Ferrari, Stefano,Gasser, Gilles
-
p. 14421 - 14436
(2015/03/30)
-
- Synthesis, docking, invitro antimicrobial and antimalarial evaluation of novel 2-(furan-3-yl)-1H-benzo [D] imidazole anchored with flavone and pyrazole derivatives
-
A series of novel substituted flavones and pyrazoles together with 2-(furan-3-yl)- 1H-benzo [d] imidazole were synthesized and evaluated for their antimicrobial and antiparastic activities. Among the synthesized compounds, 6c and 8a showed promising antib
- Gadakha, Amol V.,Sahebrao, S. Rindhe,Karale, Bhausaheb. K.
-
p. 213 - 222
(2019/01/21)
-
- SUBSTITUTED HYDRAZIDE COMPOUNDS AND USE THEREOF
-
The invention relates to substituted hydrazide compounds as shown by general formula I, including geometrical isomers, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and use of the same, wherein the substitutents Ar and R have the same meanings as given in the Description. The invention further relates to the use of compounds of general formula I in the preparation of medicament for the treatment and/or prevention of cancer and other proliferative diseases.
- -
-
-
- SUBSTITUTED HYDRAZIDE COMPOUNDS AND APPLICATION THEREOF
-
The invention relates to substituted hydrazide compounds as shown by general formula I, including geometrical isomers, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and use of the same, wherein the substitutents Ar and R having the same meanings as given in the Description. T The invention further relates to the use of compounds of general formula I in the preparation of medicament for the treatment and/or prevention of cancer and other proliferative diseases.
- -
-
-
- Characterization of Telmisartan-Derived PPARγ Agonists: Importance of Moiety Shift from Position6 to5 on Potency, Efficacy and Cofactor Recruitment
-
Selective modulation of the peroxisome proliferator-activated receptor gamma (PPARγ) by direct binding of small molecules demonstrates a promising tool for treatment of insulin resistance and type2 diabetes mellitus. Besides its blood pressure-lowering properties, the AT1-receptor blocker telmisartan has been shown to be a partial agonist of PPARγ with beneficial metabolic effects in vitro and in mice. In our previous work, comprehensive structure-activity relationship (SAR) studies discussed the different parts of the telmisartan structure and various moieties. Based on these findings, we designed and synthesized new PPARγ ligands with a benzimidazole (agonists 4-5 and 4-6), benzothiophene (agonists 5-5 and 5-6) or benzofuran (agonists 6-5 and 6-6) moiety either at position5 or6 of the benzimidazole core structure. Lipophilicity and EC50 values were improved for all new compounds compared with telmisartan. Regarding PPARγ activation, the compounds were characterized by a differentiation assay using 3T3-L1 cells and a luciferase assay with COS-7 cells transiently transfected with pGal4-hPPARgDEF, pGal5-TK-pGL3 and pRL-CMV. A decrease in both potency and efficacy was observed after the shift of either the benzothiophene or the benzofuran moiety from position6 to position5. Selective recruitment of the coactivators TRAP220, SRC-1 and PGC-1α, and release of corepressor NCoR1 determined by time-resolved fluorescence resonance energy transfer (TR-FRET) was detected depending on residues in position5 or6.
- Herbst, Lena,Goebel, Matthias,Bandholtz, Sebastian,Gust, Ronald,Kintscher, Ulrich
-
p. 1935 - 1942
(2013/01/15)
-
- Efficient synthesis of some novel macrocyclic diamides using fast addition method
-
Synthesis of some new macrocyclic diamides based on catechol scaffold by cyclization reactions between various diamines and 2-[2-(2-chloro-2-oxoethoxy) phenoxy]ethanoyl chloride using fast addition method has been described. The reactions were carried out in short reaction times and the expected macrocycles were obtained in good to high yields. Georg Thieme Verlag Stuttgart.
- Sharghi, Hashem,Zare, Abdolkarim
-
p. 999 - 1004
(2007/10/03)
-
- PIPERIDINE DERIVATIVES HAVING CCR3 ANTAGONISM
-
The invention provides low molecular compounds having activity which inhibits binding of CCR3 ligands to CCR3 on target cells, i.e. CCR3 antagonists. The invention also provides compounds represented by formula (I) below, pharmaceutically acceptable acid adducts thereof, or pharmaceutically acceptable C1-C6 alkyl adducts thereof, as well as pharmaceutical compositions comprising them as effective ingredients, which are useful for treatment or prevention of diseases associated with CCR3, such as asthma and allergic rhinitis.
- -
-
Page 438-439
(2008/06/13)
-
- Benzimidazole compounds
-
A benzimidazole compound represented by the formula (I): wherein R3is a carboxyl group, a esterified carboxyl group, an amidated carboxyl group, an amino group, an amido group, or a sulfonyl group, or their pharmaceutically acceptable salts. Because of their blood sugar-depressing effect or PDE5 inhibitory effect, these compounds or salts thereof are useful as medicines for treating impaired glucose tolerance, diabetes, diabetic complications, syndrome of insulin resistance, hyperlipidemia, atherosclerosis, cardiovascular disorders, hyperglycemia, or hypertension; or stenocardia, hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy, tubulointerstitial disorders, renal failure, atherosclerosis, angiostenosis, distal angiopathy, cerebral apoplexy, chronic reversible obstructions, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility disorders, impotence, diabetic complications, nephritis, cancerous cachexia, or restenosis after PTCA.
- -
-
Page column 83
(2010/02/05)
-
- The synthesis and evaluation of o-phenylenediamine derivatives as fluorescent probes for nitric oxide detection
-
A series of molecular probes for the determination of nitric oxide (NO) have been prepared. Each probe consists of an anthracene, coumarin or acridine fluorophore coupled to an electron rich o-phenylenediamine group. The o-phenylenediamine group can be substituted with methyl or methoxy groups to enhance its electron rich nature. The fluorophore fluorescence is quenched by photoelectron transfer (PET) from the aromatic amine to the lowest unoccupied orbital of the excited state fluorophore. Reaction with nitrosating species converts the o-phenylenediamine group into an electron deficient benzotriazole derivative. This group has a higher oxidation potential and does not quench the fluorophore fluorescence by photoelectron transfer so that these products are highly fluorescent. Some benzotriazole derivatives were made preparatively by alternative synthetic routes. The formation of fluorescent probes was evaluated by treatment of the precursors with nitrous fumes and S-nitroso-N-acetylpenicillamine (SNAP).
- Plater,Greig,Helfrich,Ralston
-
p. 2553 - 2559
(2007/10/03)
-
- Tris-benzimidazole derivatives: Design, synthesis and DNA sequence recognition
-
Two tris-benzimidazole derivatives have been designed and synthesized based on the known structures of the bis-benzimidazole stain Hoechst 33258 complexed to short oligonucleotide duplexes derived from single crystal X-ray studies and from NMR. In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent. Whereas one tris-benzimidazole carries a N-methyl-piperazine at the 6-position, the other one has this group replaced by a 2-amino-pyrrolidine ring. This latter substituent results in stronger DNA binding. The optimized synthesis of the drugs is described. The two tris-benzimidazoles exhibit high AT-base pair (bp) selectivity evident in footprinting experiments which show that five to six base pairs are protected by the tris-benzimidazoles as compared to four to five protected by the bis-benzimidazoles. The tris-benzimidazoles bind well to sequences like 5′-TAAAC, 5′-TTTAC and 5′-TTTAT, but it is also evident that they can bind weakly to sequences such as 5′-TATGTT-3′ where the continuity of an AT stretch is interrupted by a single G·C base pair.
- Ji, Yu-Hua,Bur, Daniel,H?sler, Walter,Schmitt, Valérie Runtz,Dorn, Arnulf,Bailly, Christian,Waring, Michael J.,Hochstrasser, Remo,Leupin, Werner
-
p. 2905 - 2919
(2007/10/03)
-
- Studies in Antiparasitic Agents: Part 9 - Synthesis of 5(6)-Alkoxycarbonyl-2-substituted-benzimidazoles as Potential Anthelmintics
-
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.
-
p. 1106 - 1109
(2007/10/02)
-
- Substituted 1-sulfonylbenzimidazoles
-
Certain 1-sulfonyl-2,5(6)-substituted-benzimidazole compounds are useful as antiviral agents.
- -
-
-