Category: 3012-80-4

Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity was written by Woo, Ho Bum;Eom, Young Woo;Park, Kyu-Sang;Ham, Jungyeob;Ahn, Chan Mug;Lee, Seokjoon. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A novel curcumin mimic library possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of I or II with diversely substituted benzimidazolyl-2-carbaldehydes. The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound III with IC₅₀ of 1.0 and 1.9 渭M has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, resp., and that compound IV with IC₅₀ of 1.9 渭M has a strong inhibitory effect on the growth of MCF-7 cancer cells. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Hidden signatures: new reagents for developing latent fingerprints was written by Plater, M. John;Barnes, Paul;McDonald, Lauren K.;Wallace, Sandy;Archer, Nia;Gelbrich, Thomas;Horton, Peter N.;Hursthouse, Michael B.. And the article was included in Organic & Biomolecular Chemistry in 2009.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

Aldehydes substituted with a quaternized pyridinium or quinolinium ring have been investigated for the development of latent fingerprints. Two routes were developed to a novel in situ formed azacyanine dye. This dye might form in the fingerprint where reagents are concentrated but does not form appreciably in solution experiments as evidenced by the lack of an absorption band at 600 nm. N-Alkyl and N-aryl substituted benzimidazole-2-carboxaldehydes give stable fluorescent fingerprints. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A library of novel hydroxamic acids targeting the metallo-protease family: Design, parallel synthesis and screening was written by Flipo, Marion;Beghyn, Terence;Charton, Julie;Leroux, Virginie A.;Deprez, Benoit P.;Deprez-Poulain, Rebecca F.. And the article was included in Bioorganic & Medicinal Chemistry in 2007.Synthetic Route of C9H8N2O This article mentions the following:

The authors report here the design and parallel synthesis of 217 compounds based on a malonic-hydroxamic acid template. These compounds are obtained via a two-step solution-phase procedure. The set of diverse building-blocks used makes this strategy suitable for the search of inhibitors of various metallo-proteases and for the investigation of the biol. role of new metallo-proteases. As a proof of concept, the authors screened this library on neutral aminopeptidase (APN; E.C. 3.4.11.2), the prototypal enzyme of the M1 family. Several submicromolar inhibitors were identified. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Synthetic Route of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Catalyst selection by transition state affinity chromatography-an assessment was written by Tran, Anh T.;Rapp, Jacob T.;Nicholas, Kenneth M.. And the article was included in Molecular Catalysis in 2017.Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A new method for catalyst selection-optimization is introduced and evaluated, transition state affinity chromatog. (TSAC), based on the relative chromatog. affinity of pre-catalysts for a supported-substrate vs. a transition state analog (TSA). The affinities of a library of Zn-imine complexes on three designer HPLC affinity columns that possess either an immobilized substrate, a transition state analog or a non-binding reference compound are compared to their catalytic activities for picolinate ester hydrolysis. For those Zn-complexes whose ligands possess a hydroxyalkyl side chain the retention times on the substrate-affinity column correlate linearly with the catalyst-substrate affinity, 1/K_M, derived from the kinetics of the LZn-catalyzed hydrolysis of 4-nitrophenyl picolinate. Addnl., the kinetically determined esterolytic catalytic activities, k_cat, for the hydroxyalkyl-bearing complexes also correlate with their relative chromatog. affinity on the TSA- vs sub-affinity columns. Zinc-complexes that lack the hydroxyalkyl arm, however, show no correlation of their chromatog. behavior with 1/K_M and an inverse correlation with k_cat. These results are interpreted in terms of differences in the catalytic mechanisms for the two sets of catalysts. TSAC is shown to be viable for selecting the most active esterolytic Zn-catalyst from a mixture of five complexes. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents was written by Zhang, Xiaojie;Wang, Rubing;Perez, German Ruiz;Chen, Guanglin;Zhang, Qiang;Zheng, Shilong;Wang, Guangdi;Chen, Qiao-Hong. And the article was included in Bioorganic & Medicinal Chemistry in 2016.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

In search of more effective chemotherapeutics for the treatment of castration-resistant prostate cancer and inspired by curcumin analogs, twenty five (1E,3E,6E,8E)-1,9-diarylnona-1,3,6,8-tetraen-5-ones bearing two identical terminal heteroaromatic rings have been successfully synthesized through Wittig reaction followed by Horner-Wadsworth-Emmons reaction. Twenty-three of them are new compounds The WST-1 cell proliferation assay was employed to assess their antiproliferative effects toward both androgen-sensitive and androgen-insensitive human prostate cancer cell lines. Eighteen out of twenty-five synthesized compounds possess significantly improved potency as compared with curcumin. The optimal compound, I, is 14- to 23-fold more potent than curcumin in inhibiting prostate cancer cell proliferation. It can be concluded from the data that 1,9-diarylnona-1,3,6,8-tetraen-5-one can serve as a new potential scaffold for the development of antiprostate cancer agents and that pyridine-4-yls and quinolin-4-yl act as optimal heteroaromatic rings for the enhanced potency of this scaffold. Two of the most potent compounds, II and III, effectively suppress PC-3 cell proliferation by activating cell apoptosis and by arresting cell cycle in the G₀/G₁ phase. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3鈥揅6) is higher than in water and generally decreases with a Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Metal-free oxidative decarbonylative halogenation of fused imidazoles was written by Singh, Davinder;Tali, Javeed Ahmad;Kumar, Gulshan;Shankar, Ravi. And the article was included in New Journal of Chemistry in 2021.Synthetic Route of C9H8N2O This article mentions the following:

An efficient strategy was developed for the deformylative halogenation of carbaldehyde imidazo-fused heterocycles in the presence of TBHP controlled by temperature A convenient and sequential functionalization (C8 to C3) portrayed the synthetic utility of the current method. N-Heterocycle benzamide products were also observed via the ring opening of imidazopyridines through the cleavage of C-C bond at high temperatures Features of this method included temperature-controlled excellent regioselectivity, mild conditions and functional group tolerance. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Synthetic Route of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Methylation of benzimidazole- and benzothiazolecarboxaldoximes was written by Poziomek, E. J.;Poirier, R. H.;Morin, R. D.;Page, T. F. Jr.. And the article was included in Journal of Organic Chemistry in 1963.Related Products of 3012-80-4 This article mentions the following:

Conversion of 1,2-dimethylbenzimidazole, m. 109-10掳, gave 1-methylbenzimidazole-2-carboxaldehyde, m. 107-8掳, 位 5.9 渭; oxime m. 224-5掳. The oxime (0.3 g.) kept 2 days at 20掳 with excess MeI in MeOH-EtOH gave 0.1 g. 1,3-dimethyl-2-formylbenzimidazolium iodide oxime (I), m. 204-5掳 (decomposition). Benzothiazole-2-carboxaldehyde, m. 75-6掳 (petr. ether), recrystallized from MeOH to give the hemiacetal, m. 89-91掳, gave the corresponding oxime (II), m. 168-9掳. II (11.5 g.) and 24.6 g. MeI in 75 ml. 4:1 PhNO₂-EtOH refluxed 11 hrs. and the solution kept 1 week at 20掳, filtered and the residual red-brown solid (11.0 g.) boiled in 300 ml. MeOH with activated C, the solution gradually diluted with Et₂O and cooled gave 0.4 g. N-methyl-2-formyl-3-methylbenzothiazolium iodide oxime (III, R = Me) (IV), m. 226-8掳, 7.6 g. mixture, m. 198-200掳, containing 75% 2-formyl-3-methylbenzothiazolium iodide oxime (V); and 1.0 g. V, m. 203-4掳 (decomposition), neutralization equivalent 322, pK_a 6.3 (H₂O), 位 329 m渭 (0.1N HCl), 位 363 m渭 (0.1N NaOH). The more facile synthesis of I than of V was understandable in light of the more basic center in the 1-methylbenzimidazole ring. Failure to find hydriodides III (R = H) or the MeO compound (VI, R = H) indicated that the ring N atoms were not hindered sterically to any serious extent. II (2.4 g.) and 5 ml. MeI refluxed 24 hrs. in 15 ml. MeOH and the concentrated solution diluted with Et₂O, separated from 1.3 g. solid, m. 189-90掳 (decomposition), and the filtrate evaporated, the recovered II (1.6 g.) refluxed 6 hrs. in MeOH with MeI and the product (0.3 g.) isolated, the 2 crops (1.6 g.) taken up in 100 ml. MeOH-EtOH and treated with Norit, the filtered solution concentrated to 50 ml. and cooled yielded 28% V. II (5.0 g.) in 100 ml. hot MeOH treated with 8 g. MeONH₂.HCl and the mixture heated 30 min. on a steam bath, diluted to incipient cloudiness, and cooled gave 4.6 g. O-methylbenzothiazole-2-carboxaldoxime, m. 65-8掳, converted (4.0 g.) by refluxing 85 hrs. with 10 ml. MeI in 75 ml. MeOH and diluting the cooled mixture with Et₂O to give 0.6 g. orange VI (R = Me). Similarly II was converted by use of HONHMe.HCl to give 26% IV, m. 233-5掳, exhibiting an infrared spectrum identical with the side-product isolated in the methylation of II. The nuclear magnetic resonance spectrum of I in D₂O gave a singlet at 522 cycles/sec., a sym. multiplet at 468 cycles/sec., and a single sharp peak at 249 cycles/sec. The :NOH proton resonance at 740 cycles/sec. was observed in redistilled dry MeCN. Structure proof of V was achieved on the basis of elemental analyses, neutralization equivalent, and infrared and ultraviolet spectral observations. I, pK_a 7.0, and V, pK_a 6.3, are the most acidic of the reported heterocyclic aldoxime methiodides. The low pK_a of I relative to the high basicity of its heterocyclic nucleus was discussed in terms of configuration and ring substitution position. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Related Products of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Related Products of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

New (E)-1-alkyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies was written by Sharma, Pankaj;Thummuri, Dinesh;Reddy, T. Srinivasa;Senwar, Kishna Ram;Naidu, V. G. M.;Srinivasulu, Gannoju;Bharghava, Suresh K.;Shankaraiah, Nagula. And the article was included in European Journal of Medicinal Chemistry in 2016.Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A new series of (E)-[(benzo[d]imidazol-2-yl)methylene]indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 8l (I) showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC₅₀ values of 3.26 卤 0.24 渭M and 5.96 卤 0.67 渭M resp. The compounds 8f (II), 8i (III), 8l (I) and 8o (IV) were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 8l led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry anal. reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 8l induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 8l treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem