Tag: M.W=150-200

Qiao, Baokun published the artcileOrganocatalytic Asymmetric Michael Addition of 5H-Oxazol-4-ones to Nitroolefins, Category: nitriles-buliding-blocks, the publication is Organic Letters (2013), 15(10), 2358-2361, database is CAplus and MEDLINE.

The first organocatalytic asym. Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst I, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral α-alkyl-α-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biol. active compounds

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kim, Michelle B. published the artcileThe Synthesis and Antimicrobial Activity of Heterocyclic Derivatives of Totarol, Quality Control of 5653-62-3, the main research area is totarol heterocyclic derivative preparation antimicrobial.

The synthesis and antimicrobial activity of heterocyclic analogs of the diterpenoid totarol, e.g., I, are described. An advanced synthetic intermediate with a ketone on the A-ring is used to attach fused heterocycles, and a carbon-to-nitrogen atom replacement is made on the B-ring by de novo synthesis. A-ring analogs with an indole attached exhibit, for the first time, enhanced antimicrobial activity relative to the parent natural product. Preliminary experiments demonstrate that the indole analogs do not target the bacterial cell division protein FtsZ as had been hypothesized for totarol.

ACS Medicinal Chemistry Letters published new progress about Antibacterial agents. 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Quality Control of 5653-62-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bergeron, Raymond J. published the artcilePartition-Variant Desferrithiocin Analogues: Organ Targeting and Increased Iron Clearance, Formula: C9H9NO2, the main research area is desferrithiocin analog organ targeting iron clearance.

Altering the lipophilicity (log Papp) of desferrithiocin analogs can change the organ distribution of the chelators and lead to enhanced iron clearance. For example, alkylation of (S)-2-(2,4-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-4′-(HO)-DADFT] and its analogs to more lipophilic compounds, such as (S)-4,5-dihydro-2-(2-hydroxy-4-methoxyphenyl)-4-methyl-4-thiazolecarboxylic acid [(S)-4′-(CH3O)-DADFT], provides ligands that achieved between a 3- and 8-fold increase in chelator concentrations in the heart, liver, and pancreas (the organs most at risk in iron-overload disease) of treated rodents. The 4′-O-methylated compounds are demethylated to their hydroxylated counterparts in rodents; furthermore, this O-demethylation takes place in both rodent and human liver microsomes. The relationship between chelator lipophilicity and iron-clearing efficacy in the iron-overloaded Cebus apella primate is further underscored by a comparison of the iron-clearing efficiency of (S)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-3′-(HO)-DADFT] and its 3′-(CH3O) counterpart. Finally, these DFT analogs are shown to be both inhibitors of the iron-mediated oxidation of ascorbate as well as effective radical scavengers.

Journal of Medicinal Chemistry published new progress about Biological transport. 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Formula: C9H9NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Al-Hamdany, Raad published the artcileDiels-Alder reaction of o-benzoquinone, Product Details of C9H9NO2, the main research area is Diels Alder benzoquinone cyclopentadiene; regiochemistry Diels Alder benzoquinone.

Diels-Alder reaction between o-benzoquinones carrying an electron withdrawing group at position 3 and cyclopentadiene are reported. In these reactions the quinone behaves as a dienophile, but afforded a monoadduct I (R = CHO, COMe, CN, CO2Me, COPh), which resulted from the addition of cyclopentadiene abnormally to the unsubstituted side of the quinone.

Journal of the Iraqi Chemical Society published new progress about Diels-Alder reaction. 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Product Details of C9H9NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Huang, Yunsheng published the artcileSynthesis of 2-(2,3-dimethoxyphenyl)-4-(aminomethyl)imidazole analogues and their binding affinities for dopamine D2 and D3 receptors, Name: 2,3-Dimethoxybenzonitrile, the main research area is imidazolemethanamine dimethoxyphenyl bromodimethoxyphenyl preparation dopamine receptor; imidazolylmethyl methoxyisoquinoline preparation dopamine receptor.

A series of 2-(2,3-dimethoxyphenyl)-4-(aminomethyl)imidazole derivatives was prepared and their affinity for dopamine D2 and D3 receptors was measured using in vitro binding assays. Several oxadiazole analogs were also prepared and tested for their affinity for dopamine D2 and D3 receptors. The results of receptor binding studies indicated that the incorporation of an imidazole moiety between the Ph ring and the basic nitrogen did not significantly increase the selectivity for dopamine D3 receptors, whereas the incorporation of an oxadiazole at the same region resulted in a total loss of affinity for both dopamine receptor subtype binding sites. The most selective compound in this series is 6,7-dimethoxy-2-[[2-(2,3-dimethoxyphenyl)-1H-imidazol-4-yl]methyl]-1,2,3,4-tetrahydroisoquinoline, which has a D3 receptor affinity of 21 nM and a 7-fold selectivity for D3 vs. D2 receptors. The binding affinity for σ1 and σ2 receptors was also measured, and the results showed that several analogs were selective σ1 receptor ligands.

Bioorganic & Medicinal Chemistry published new progress about Dopamine antagonists. 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Name: 2,3-Dimethoxybenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wong, Ying-Chieh published the artcileLewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide, Application In Synthesis of 97009-67-1, the main research area is electrophilic bromocyclization cyclopropylmethyl amide Lewis base sulfide catalyst; oxazoline oxazine stereoselective preparation.

A Lewis basic sulfide catalyzed electrophilic bromocyclization of cyclopropylmethyl amide has been developed. The catalytic protocol is applicable to both 1,1- and 1,2-substituted cyclopropylmethyl amides, giving oxazolines and oxazines, e.g. I and II, in good yields and excellent diastereoselectivity.

Organic Letters published new progress about Cyclization catalysts. 97009-67-1 belongs to class nitriles-buliding-blocks, name is 1-(4-Fluorophenyl)cyclopropanecarbonitrile, and the molecular formula is C10H8FN, Application In Synthesis of 97009-67-1.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kulkarni, Bheemashankar A. published the artcileA solid-phase equivalent of van Leusen’s TosMIC, and its application in oxazole synthesis, Application of 4-(5-Oxazolyl)benzonitrile, the main research area is solid phase synthesis aryloxazole; oxazole aryl solid phase synthesis.

Polystyrene-SH resin, prepared from Merrifield resin in two steps, was converted to polystyrene-SO2-CH2-NC in three steps. This resin functions as a solid-phase equivalent of p-tolylsulfonylmethyl isocyanide (TosMIC). Thus, reaction with aromatic aldehydes and tetrabutylammonium hydroxide as base yields 5-aryloxazoles.

Tetrahedron Letters published new progress about Solid phase synthesis. 87150-13-8 belongs to class nitriles-buliding-blocks, name is 4-(5-Oxazolyl)benzonitrile, and the molecular formula is C10H6N2O, Application of 4-(5-Oxazolyl)benzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fernandez, Maria-Carmen published the artcileDesign, synthesis and structure-activity-relationship of 1,5-tetrahydronaphthyridines as CETP inhibitors, Application of 3-Formyl-5-(trifluoromethyl)benzonitrile, the main research area is tetrahydronaphthyridine preparation CETP inhibitor structure activity relationship.

This Letter describes the discovery and SAR optimization of 1,5-tetrahydronaphthyridines, a new class of potent CETP inhibitors. The effort led to the identification of I and II with in vitro human plasma CETP inhibitory activity in the nanomolar range (IC50 = 23 and 22 nM, resp.). Both I and II exhibited robust HDL-c increase in hCETP/hApoA1 dual heterozygous mice model.

Bioorganic & Medicinal Chemistry Letters published new progress about Cardiovascular disease. 569370-39-4 belongs to class nitriles-buliding-blocks, name is 3-Formyl-5-(trifluoromethyl)benzonitrile, and the molecular formula is C9H4F3NO, Application of 3-Formyl-5-(trifluoromethyl)benzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hynes, John B. published the artcileDirect synthesis of 2,4-diaminoquinazolines from 2-fluorobenzonitriles, Category: nitriles-buliding-blocks, the main research area is quinazoline diamino derivative preparation; diaminoquinazoline derivative preparation; difluorobenzonitrile cyclocondensation guanidine carbonate; fluorobenzonitrile cyclocondensation guanidine carbonate.

In a search for new methods for preparing 2,4-diaminoquinazolines I (R = 5-F, 5-Cl, 5-Br, 5-I, 6-F, 7-F, 8-F, 5-OMe, 5-SMe, 5-NMe2, 5,6,7,8-F4) it was found that the reaction of 2,6-difluorobenzonitrile with guanidine carbonate gave 2,4-diamino-5-fluoroquinazoline (I; R = 5-F) in excellent yield. Extension of this approach to other 2-fluorobenzonitriles, some of which were elaborated for the first time, showed that this reaction possesses considerable generality. The cyclization was successful even when electron donating groups were present at C(6). Only in 2 cases where a primary or secondary amino group was also present ortho to the cyano group was this transformation unsuccessful.

Journal of Heterocyclic Chemistry published new progress about Cycloaddition reaction. 119584-73-5 belongs to class nitriles-buliding-blocks, name is 2-Ethoxy-6-fluorobenzonitrile, and the molecular formula is C9H8FNO, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Le, Thanh Nguyen published the artcileNovel synthesis of the natural protoberberine alkaloids: oxypalmatine and oxypseudopalmatine, Name: 2-Formyl-4,5-dimethoxybenzonitrile, the main research area is oxypalmatine oxypseudopalmatine protoberberine alkaloid synthesis cycloaddition nucleophilic substitution.

Oxypalmatine (I) and oxypseudopalmatine (II) were synthesized in three steps from the benzonitrile III and toluamides IV (R1 = OMe, R2 = H; R1 = H, R2 = OMe, resp.). The lithiated cycloaddition reaction yielded 3-arylisoquinolinone intermediates. A subsequent internal SN2 reaction produced the corresponding 8-oxoprotoberberines, oxypalmatine and oxypseudopalmatine.

Bulletin of the Korean Chemical Society published new progress about Cycloaddition reaction. 1013112-48-5 belongs to class nitriles-buliding-blocks, name is 2-Formyl-4,5-dimethoxybenzonitrile, and the molecular formula is C10H9NO3, Name: 2-Formyl-4,5-dimethoxybenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts