- Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes
-
CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.
- Dong, Yaxi,Breit, Bernhard
-
p. 6765 - 6769
(2021/09/11)
-
- Benzimidazole derivatives as potent and isoform selective tumor-associated carbonic anhydrase IX/XII inhibitors
-
We describe the synthesis of a series of 2-arylbenzimidazole derivatives bearing sulfonamide functionality (4a–d, 7a–c and 10) as well as hydroxamic acid (15a–b), carboxylic acid (16a–b), carboxamide (17a–b) and boronic acid (22a–b and 26) functionalities, which act as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. The newly synthesized benzimidazole derivatives were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IX, and XII), and especially the sulfonamide-containing benzimidazoles demonstrated intriguing inhibitory activity against tumor associated CA IX and XII with KI values in the range of 5.2–29.3 nM and 9.9–41.7 nM, respectively. Notably, compound 4c was the most potent and selective CA IX (KI = 6.6 nM) and XII (KI = 9.9 nM) inhibitor with a significant selectivity ratio over cytosolic CA I and II isoforms in the range of 3.4–25.2. In addition, compounds having hydroxamic acid (15a-b) or carboxylic acid (16a-b) functionalities resulted in greater selectivity ratios for CA IX/XII over CAI/II in the range of 4.1–121.5 although with KI values in lower micromolar potency (KIs = 0.36–0.85 μM for CA IX/XII).
- ?al??kan, Burcu,Banoglu, Erden,Gür Maz, Tu??e,Nocentini, Alessio,Supuran, Claudiu T.,Uslu, Azize Gizem
-
-
- STING AGONISTS AND USES THEREOF
-
The present invention provides compounds, compositions thereof, and methods of using the same for the modulation of STING, and the treatment of STING-mediated disorders.
- -
-
Paragraph 00717
(2020/07/14)
-
- The discovery of new scaffold of plant activators: From salicylic acid to benzotriazole
-
Started from salicylic acid (SA) and related commercialized plant activators, based on molecular three-dimensional shape and pharmacophore similarity comparison (SHAFTS), a new lead compound benzotriazole was predicted and a series of benzotriazole derivatives were designed and synthesized. The bioassay showed that benzotriazole had high activity against a broad spectrum of diseases including fungi and oomycetes in vivo, but no activity in vitro. And the introduction of proper groups at the 1’-position and 5’-position was beneficial to the activity. So, they had the potential to be exploited as novel plant activators.
- Chang, Kang,Chen, Jian-Qin,Shi, Yan-Xia,Sun, Mei-Jian,Li, Peng-Fei,Zhao, Zhen-Jiang,Zhu, Wei-Ping,Li, Hong-Lin,Xu, Yu-Fang,Li, Bao-Ju,Qian, Xu-Hong
-
p. 919 - 926
(2017/05/16)
-
- BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS
-
Compounds of formula (I): wherein X, Y, R1 and R3-R11 are as herein defined, and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.
- -
-
Page/Page column 108; 109
(2016/12/07)
-
- 2-(AZAINDOL-2-YL)BENZIMIDAZOLES AS PAD4 INHIBITORS
-
Compounds of formula (I): wherein; R1 is hydrogen or C1-6alkyl;R2 is hydrogen, C1-6alkyl, perhalomethylC0-5alkyl-O—, or C1-6alkoxy;R3 is hydrogen, C1-6alkyl, or C1-6alkoxyC1-6alkyl;R4 is hydrogen, C1-6alkyl, perhalomethylC1-6alkyl; or unsubstituted C3-6cycloalkylC1-6 alkyl;A is C—R5 or N;B is C—R6 or N;D is C—R7 or N;with the proviso that at least one of A, B, and D, is N;R5 is hydrogen or C1-6alkyl;R6 is hydrogen or C1-6alkyl;R7 is hydrogen, C1-6alkyl, C1-6alkoxy, or hydroxy;R8 is hydrogen or C1-6alkyl, with the proviso that one of R4 and R8 is hydrogen;R9 is hydrogen or hydroxy;R10 is hydrogen or C1-6alkyl; and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.
- -
-
Paragraph 0389; 0390; 0391
(2015/07/02)
-
- 2-(4-ARYL-1H-IMIDAZOL-1-YL)ANILINE COMPOUNDS
-
The present invention provides compounds that are useful as vaccine adjuvants and/or antitumor agents and methods for producing and using the same. In one particular aspect of the invention, compounds of the invention are of the formula (I) where R1, R2, R3 and Ar1 are those defined herein.
- -
-
Paragraph 0068; 0107
(2015/11/27)
-
- 2 - (AZAINDOL- 2 -YL) BENZ IMIDAZOLES AS PAD4 INHIBITORS
-
Compounds of formula (I) wherein; R1 is hydrogen or C1-6alkyl; R2 is hydrogen, C1-6alkyl, perhalomethylC0-5alkyl-O-, or C1-6alkoxy; R3 is hydrogen, C1-6alkyl, or C1-6alkoxyC1-6alkyl; R4 is hydrogen, C1-6alkyl, perhalomethylC1-6alkyl; or unsubstituted C3-6cycloalkylC1-6alkyl; A is C-R5 or N; B is C-R6 or N; D is C-R7 or N; with the proviso that at least one of A, B, and D, is N; R5 is hydrogen or C1-6alkyl; R6 is hydrogen or C1-6alkyl; R7 is hydrogen, C1-6alkyl, C1-6alkoxy, or hydroxy; R8 is hydrogen or C1-6alkyl, with the proviso that one of R4 and R8 is hydrogen; R9 is hydrogen or hydroxy; R10 is hydrogen or C1-6alkyl; and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.
- -
-
Page/Page column 50
(2014/02/16)
-
- Substituted Pyran Derivatives
-
Certain 3,6-disubstituted and 2, 4, 5-trisubstituted pyran derivatives that exhibit potent activity on monoamine transport systems are provided. The 3, 6 and 2, 4, 5 pyrans are useful in probing the effects of their binding to monoamine transporter system
- -
-
Paragraph 0166; 0167
(2014/10/29)
-
- When inhibitors do not inhibit: Critical evaluation of rational drug design targeting chorismate mutase from mycobacterium tuberculosis
-
Tuberculosis (TB) is a devastating disease that claims millions of lives every year. Hindered access or non-compliance to medication, especially in developing countries, led to drug resistance, further aggravating the situation. With current standard ther
- Munack, Steffi,Leroux, Vincent,Roderer, Kathrin,?kvist, Mats,Van Eerde, André,Gundersen, Lise-Lotte,Krengel, Ute,Kast, Peter
-
p. 2507 - 2527
(2013/01/16)
-
- Substituted Fused Imidazole Derivatives, Pharmaceutical Compositions, and Methods of Use Thereof
-
Substituted fused imidazole derivatives, methods of their preparation, pharmaceutical compositions comprising a substituted fused imidazole derivative, and methods of use in treating inflammation are provided. The substituted fused imidazole derivatives may control the activity or the amount or both the activity and the amount of heme-oxygenase.
- -
-
Page/Page column 117-118
(2011/09/14)
-
- SUBSTITUTED BENZIMIDAZOLES, BENZOTHIAZOLES AND BENZOXAZOLES
-
The present invention relates to substituted benzimidazoles, benzothiazoles and benzoxazoles, processes for their preparation, medicaments containing these compounds and the use of these compounds for the preparation of medicaments.
- -
-
Page/Page column 112
(2010/12/29)
-
- 3H-IMIDAZO [4, 5 -C] PYRIDINE- 6 -CARBOXAMIDES AS ANTI- INFLAMMATORY AGENTS
-
The present invention relates to compounds of general formula (I) in which A, L, M, Q2, Q3, Q4, R1, R5, Ra, Rb, Rc, W, X, Y, Z1, Z2, Z3 are defined in the description, the salts thereof, particularly the physiologically acceptable salts thereof. The compounds are of potential utility in the treatment and/or prevention of inflammatory diseases and associated conditions, in particular, in the treatment and/or prevention of pain. The invention also relates to the use of such compounds as medicaments, to pharmaceutical compositions containing them, and to their preparation.
- -
-
Page/Page column 82
(2010/09/18)
-
- SPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS
-
The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating mammals suffering from the condition of being overweight.
- -
-
Page/Page column 32-33; 38-40
(2008/12/06)
-
- BENZIMIDAZOLE ANTAGONISTS OF THE H-3 RECEPTOR
-
This invention is directed to a compound of formula (I), as defined herein, or a pharmaceutically acceptable salt thereof; a pharmaceutical composition containing a compound of formula (I), a process of preparation of a compound of formula (I), a method o
- -
-
Page/Page column 33
(2010/11/27)
-
- Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups
-
A series of benzimidazole-5-carboxylic acid alkyl ester derivatives carrying amide or amidine substituted methyl or phenyl groups at the position C-2 were synthesised and evaluated for antibacterial and antifungal activities against S. aureus, methicillin
- Oezden, Seckin,Atabey, Dilek,Yildiz, Sulhiye,Goeker, Hakan
-
p. 1587 - 1597
(2007/10/03)
-
- COMPOUND INHIBITING DIPEPTIDYL PEPTIDASE IV
-
The invention aims to provide a dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. The invention is directed to a compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or -COOR5 whereupon R5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R1 and R2, together with a carbon atom to which they are bound, represent a 3- to 6-membered cycloalkyl group, R3 represents hydrogen or an optionally substituted C6-10 aryl group, R4 represents a hydrogen or a cyano group, D represents -CONR6-, -CO- or -NR6CO-, R6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents -(CH2)m- whereupon m is an integer of 1 to 3, -CH2OCH2-, or -SCH2-, n is an integer of 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.
- -
-
Page/Page column 26
(2010/02/14)
-
- 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.
- -
-
-
- COMPOUNDS HAVING A FUSED, BICYCLIC MOIETY FOR BINDING TO THE MINOR GROOVE OF DSDNA
-
The present invention is directed to the means by which to alter the binding affinity and/or specificity of a compound with a sequence of DNA in the minor groove of a double-strand thereof. More particularly, the present invention is directed to a synthetic and/or non-naturally occurring compound (e.g., an analog of a polyamide oligomer or polymer) which contains at least one hydrogen bond donor moiety and at least one hydrogen bond acceptor moiety, wherein the latter moiety or "building block" has a fused, bicyclic structure which is heteroaromatic, said structure having a heteroatom therein which acts as a hydrogen bond acceptor to bind guanine in the minor groove of the dsDNA sequence, and which is incapable of forming a tautomer. In one particular embodiment of the synthetic and/or non-naturally occurring compound, the fused, bicyclic structure occupies an initial or first terminal position within the compound.
- -
-
-
- Efficient solution phase synthesis of 2-(N-acyl)-aminobenzimidazoles
-
An efficient solution phase protocol for the synthesis of 2-(N-acyl)-aminobenzimidazoles is reported. The 2-(N-acyl)-aminobenzimidazole ring system was assembled using SNAr reactions, nitro group reduction, acylthiourea formation and cyclization with EDC. The acyl protected 2-aminobenzimidazole derivatives were obtained in high yield and purity without purification of intermediates or final products. This reaction sequence eliminates the use of highly toxic cyanogen bromide, a reagent commonly used to prepare the 2-aminobenzimidazole ring system.
- Seth, Punit P.,Robinson, Dale E.,Jefferson, Elizabeth A.,Swayze, Eric E.
-
p. 7303 - 7306
(2007/10/03)
-
- Synthesis of some novel tetrahydronaphthalene benzimidazole derivatives
-
Retinoids, synthetic and natural analogues of all-trans-retinoic acid (RA), exert their biological effects with responsive elements of DNA to promote on cell differentiation and proliferation and behave as potent adipogenic hormones. Herein, we describe the synthesis of a number of novel tetrahydrotetramethylnaphthalene benzimidazole derivatives as retinoids. Analogs were prepared as depicted in Scheme 1 and 2. As is evident from both shemes, a variety of tetrahydrotetramethylnaphthalene benzimidazole derivatives have been synthesized by using an appropiate NaHSO3 addiction product.
- Ates-Alagoz, Zeynep,Buyukbingol, Erdem
-
p. 455 - 460
(2007/10/03)
-