Tag: M.W=100-150

Melin, Lea; Gesner, Emily; Attwell, Sarah; Kharenko, Olesya A.; van der Horst, Edward H.; Hansen, Henrik C.; Gagnon, Alexandre published the artcile< Design and Synthesis of LM146, a Potent Inhibitor of PB1 with an Improved Selectivity Profile over SMARCA2>, COA of Formula: C8H8N2O, the main research area is LM146 quinazolin synthesis anticancer SAR PB1 bromodomain.

PB1 is a bromodomain-containing protein hypothesized to act as the nucleosome-recognition subunit of the PBAF complex. Although PB1 is a key component of the PBAF chromatin remodeling complex, its exact role has not been elucidated due to the lack of potent and selective inhibitors. Chem. probes that target specific bromodomains within the complex would constitute highly valuable tools to characterize the function and therapeutic pertinence of PB1 and of each of its bromodomains. Here, we report the design and synthesis of lead compound LM146, which displays strong stabilization of the second and fifth bromodomains of PB1 as shown by DSF. LM146 does not interact with bromodomains outside of sub-family VIII and binds to PB1(2), PB1(5), and SMARCA2B with KD values of 110, 61, and 2100 nM, resp., providing a ~34-fold selectivity profile for PB1(5) over SMARCA2.

ACS Omega published new progress about Antitumor agents. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, COA of Formula: C8H8N2O.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cai, Yue-Ming; Zhang, Xin; An, Cui; Yang, Ye-Fei; Liu, Wei; Gao, Wen-Xia; Huang, Xiao-Bo; Zhou, Yun-Bing; Liu, Miao-Chang; Wu, Hua-Yue published the artcile< Catalyst-free oxidative N-N coupling for the synthesis of 1,2,3-triazole compounds with tBuONO>, Reference of 38487-85-3, the main research area is benzotriazinone preparation; aminobenzamide coupling; benzothiadiazole preparation; aminothiol N S coupling; triazolopyridine preparation; pyridinyl methanamine coupling.

A catalyst-free method was developed to synthesize 1,2,3-benzotriazinones I [R = H, 6-Cl, 6-Br, etc.] and 1,2,3-benzothiadiazoles II [R1 = H, 6-Cl, 6-Br, etc.] from 2-amino-benzamides and 2-amino thiols. Of particular note was that the one-step synthesis route to access [1,2,3]triazolo[1,5-a]pyridines III [R2 = H, Ph, 4-ClC6H4; R3 = H, 7-Me, 7-Br] from pyridin-2-ylmethanamine was reported for the first time. This approach featured no use of catalyst, extremely mild conditions and excellent efficiency.

Organic Chemistry Frontiers published new progress about Amino thiols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Reference of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hora, J. published the artcile< The synthesis of bis-endo-2-(hydroxymethyl)-5-(4-imidazolylmethyl)bicyclo[2.2.2]octane and the corresponding cyclohexane analog>, Product Details of C6H11NO2, the main research area is bicyclooctane imidazolylmethyl; cyclohexane imidazolylmethyl; imidazole bicyclooctanyl; cyclization aminoacetal.

The imidazolylbicyclooctane I was prepared in 9 steps by cyclization of 3,4-dihydrobenzoic acid with H2C:CHCO2Me and conversion of the II (R = CO2H, R1 = CO2Me) to II (R = tetrahydropyranyl, R1 = CH2Br) which was treated with Mg and (EtO)2CHCN, followed by reduction formylation, cyclization with HCONH2. 3-Oxabicyclononane was treated with MeCOCl and the cis-1-(chloromethyl)-4-(hydroxymethyl)cyclohexane similarly converted to III.

Recueil des Travaux Chimiques des Pays-Bas published new progress about Cyclization. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Product Details of C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dai, Weixiang; Petersen, Jeffrey L.; Wang, Kung K. published the artcile< Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles>, Related Products of 89324-17-4, the main research area is camptothecin ABCD ring core preparation nitrogen alkylation Curran’s protocol; intramol hetero Diels Alder acetylene allene rearrangement radical cyclization; radical cyclization reaction mechanism camptothecin core preparation; crystal mol structure indolizinoquinolinone camptothecin ring core analog.

A new synthetic pathway to the parent and substituted ABCD ring cores, e.g. I, of the camptothecin family of alkaloids was developed. The N-alkylation of 1,6-dihydro-6-oxo-2-pyridinecarbonitrile with 3-bromo-1-phenylpropyne provided II using Curran’s protocol. Treatment of II with a catalytic amount of DBU (5 mol %) at 110 °C for 12 h produced indolizino[1,2-b]quinolin-9(11H)-one (I), the parent ABCD ring core of camptothecin, in essentially quant. yield.

Organic Letters published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Related Products of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fache, F.; Cros, F.; Piva, O.; Lefebvre, F. published the artcile< Easy access to 2-alkyl and 2-arylthiazolines using a modified heteropolyacid catalysis: application to the synthesis of bacillamide A>, Synthetic Route of 6136-93-2, the main research area is thiazoline preparation microwave irradiation; aminothiol nitrile cyclization phosphotungstic acid catalyst.

A straightforward access to 2-alkyl and 2-arylthiazolines by condensation of β-aminothiols on nitriles, catalyzed by phosphotungstic acid (2%) under microwave irradiation, is described. This method has been directly applied to a short and efficient synthesis of bacillamide A.

Synthetic Communications published new progress about Heterocyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Synthetic Route of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Murakami, Teiichi; Otsuka, Masami; Ohno, Masaji published the artcile< An efficient synthesis of 5-diethoxymethylimidazole-4-carboxylate: a potential precursor for various imidazole derivatives>, Name: 2,2-Diethoxyacetonitrile, the main research area is ethoxymethylimidazolecarboxylate; imidazolecarboxylate diethoxymethyl; cycloaddition ethoxyacetonitrile methyl isocyanoacetate; nitrile cycloaddition methyl isocyanoacetate.

The title imidazolecarboxylate I [R = CH(OEt)2] was prepared in 82% yield by cycloaddition reaction of (EtO)2CHCN with CNCH2CO2Me in diglyme containing KH at 0-70° for 5 h. I [R = (MeO)3C, Ph, pyridyl, furyl] were similarly prepared in 13-85% yield.

Tetrahedron Letters published new progress about Cycloaddition reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mettry, Magi; Moehlig, Melissa P.; Hooley, Richard J. published the artcile< Synthesis, Guest Binding, and Metal Coordination of Functionalized Self-Folding Deep Cavitands>, Quality Control of 6136-93-2, the main research area is cavitand self folding preparation guest binding metal coordination.

A simple method to introduce donor functions to the upper rim of self-folding benzimidazole-based deep cavitands is described. The upper rim donors allow controlled noncovalent binding of suitably sized guest species via both self-complementary hydrogen bonding and space-filling interactions; and metal-mediated self-folding is possible if bidentate coordinators are incorporated.

Organic Letters published new progress about Cavitands Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Quality Control of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sheng, Hui-Yang; Chen, Hui; Liao, Meng; Peng, Na; Yang, Mian; Cai, Qun; Liu, Yi published the artcile< Copper-catalyzed Tandem Cyclization to Access 4-Aminoquinoline Derivatives>, SDS of cas: 38487-85-3, the main research area is nitroethenylaryl aminobenzonitrile copper catalyst tandem Michael heterocyclization oxidation; nitro arylquinolinamine preparation.

An efficient and practical method for the synthesis of 4-aminoquinoline derivativeswas developed via copper-catalyzed cascade cyclization of 2-aminobenzonitrile and nitroolefins. This reaction proceeded through a consecutive Michael addition/cyclization/oxidization protocol, providing 4-aminoquinolines with moderate to excellent yields under mild conditions. This method features readily available materials, one-pot one-step operation, and proceeded without bases.

Chemistry Letters published new progress about Alkenes, nitro Role: RCT (Reactant), RACT (Reactant or Reagent). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, SDS of cas: 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chiang, Ming-Chien; Tai, Tsui-Chen published the artcile< A quantitative relation between molecular structure and chemical reactivity. III. Addition reaction of aliphatic nitriles and methanol>, Formula: C6H11NO2, the main research area is .

The addition of MeOH to aliphatic nitriles with NaOMe as catalyst was studied. The % conversion of the nitriles plotted vs. the inductive index I for the alkyl groups in their mols. constitute a “”sigmoid”” curve, while the logs of the rate and equilibrium constants for the addition gave straight lines when plotted, resp., against the corresponding I. From the position of the point corresponding to 50% conversion on the sigmoid curve, it can be shown that the % conversion for all the aliphatic nitriles in this reaction would be very low and the reaction would proceed very slowly. α-Substituted (halogen, CO2H, CN) nitriles would undergo reaction very rapidly with very high % conversion. When the substituents are beyond the γ-position, however, the % conversion and the reaction rate would be very close to those of the simple aliphatic nitriles. The direction of turning of the sigmoid curve vs. % conversion and the direction of inclination of the straight lines vs. the rate and equilibrium constants demonstrate that this reaction is a nucleophilic addition of MeOH to aliphatic nitriles.

Huaxue Xuebao published new progress about Addition reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Meerwein, Hans; Hederich, Volker; Morschel, Hans; Wunderlich, Klaus published the artcile< Intermolecular anion transfer during organic reactions>, Formula: C6H11NO2, the main research area is .

A class of reaction mechanisms, RA + R’+ → R’A + R+, is considered, where R+ is the more stable carbonium ion, A = hydride, cyanide, or alkoxide; isolation of the R+ salts is attempted. Ph3C+ is chosen as R’+ and prepared by stirring 44.5 g. BF3-EtOAc, b13 49-51°, into 61 g. Ph3COEt in 170 cc. EtOAc with exclusion of H2O and alc., separation of Ph3CBF3 (I) by filtering after 24 hrs., and washing with low-boiling petroleum; total yield after recovery of 2nd crop 90%, m. 197-8°. Addition of 7.4 g. 1,3-dioxolane to 16.5 g. I in 60 cc. liquid SO2 under reflux (dry ice condenser) results in hydride transfer and, after evaporation and treatment with CH2Cl2 and Et2O, isolation of 88.5% 1,3-dioxolenium fluoborate, m. 83°; β-iodoethyl formate b15 65-70°, prepared with NaI in MeCN. From the CH2Cl2 washings, 58% Ph3CH, m. 90.5-1.5°, is isolated. Similarly, 2-methyl-1,3-dioxolane, the 2-Ph compound (II), and the 2,4,4,5,5-Me5 compound yield, resp., 84, 83, and 77% Ph3CH, and 69, 100, and 76% (m. 150-2°) dioxolenium fluoborates. In order to substitute for I the nonexistent Et +, 9.5 g. (Et3O) (BF4) and 9 g. II is heated to 40°, 81% Et2O distilled, and 50% II-BF4 salt and C2H6 isolated. Another H- donor is (PhCH2)3N, reacting with I in MeCN at 40-50° to yield 84% Ph3CH and 94% benzylidenedibenzylimonium fluoborate, m. 132-4°, hydrolyzed in hot 30% NaOH to (PhCH2)2NH. Cyanide transfer occurs by cooling 5 g. 2-cyano-2-methyl-1,3-dioxolane (III) in 25 cc. MeCN with 14.5 g. I, filtering off after 1 hr. 6.5 g. Ph3CCN, m. 128.6-29° (total yield 82%), and adding Et2O to isolate 59% 2-methyldioxolenium fluoborate (IV), m. 162-4°, and recover more Ph3CCN from the filtrate. III reacts with (EtO)2CHBF4, m. 20°, in CH2Cl2 to yield 88% IV and 81% (EtO)2CHCN, b760 163-4°, b15 58-9.5°, n20D 1.3978. Alkoxide transfer is reversible and usually more rapid than hydride transfer. Camphor diethyl acetal, b10 99.5-101°, (18 g.) added to 16.5 g. I in 25 cc. MeCN precipitates 95% O-ethylcamphoroxonium fluoborate, decomposed at 104-5%, isolated by washing with Et2O; 90% Ph3COEt (V), m. 82°, is obtained by evaporation of the filtrate. Similar high-yield reactions of ROEt with I or HC(OEt)2BF4 (VI) give the R salt and V or HC(OEt)3 for R = O.CH2.CH2.O.CMe (both I and VI), C(OEt)3 (both I and VI), O.CMe2.CMe2.O.CH (I only), O.CHMe.CHMe.O.CH (I only), HC(OEt)2 (Ph3CSbCl6), Me2NCHOEt [Ph3CSbCl6, VI, and HC(OEt)2SbCl6]. V is cleaved by R’BF4 (R’ = 2-methyl-, 4,5-dimethyl-, or 2,4,4,5,5-pentamethyldioxolenium) with isolation of Ph3CH and AcH. With ROEt (R = O.CH2.CH2.CH), I in CH2Cl2 yields 88% RBF4 and 95% Ph3CH, but in MeCN the same reaction produces 91% Ph3COCH2CH2COCPh3 (VII), m. 188-9° (MeCOEt), and by attack on O and ring cleavage, some RBF4, and VI. When not isolated, VII decompose to Ph3CH. RBF4 in turn reacts with V in MeCN to yield 33% VII, and VII with VI in CH2Cl2 to yield 75% RBF4. From 13.2 g. I in 20-25 cc. dry CH2Cl2, treated with 8.5 g. RNMe2 (R = O.CH2.CH2.O.CMe), b. 142°, with cooling and stirring 30 min. after slow addition, Et2O precipitates [RN(CPh3)Me2]BF4, stable, m. 170°; the iodide, obtained by treatment with NaI in MeCN, decompose at 110° to 88.5% AcNMe2, b30 76-7°, recovered by distillation, and 78.6% ICH2CH2OCPh3, m. 136-7°, obtained by crystallization of the residue from alc. or MeCN. The ether is obtained independently for comparison from Ph3CH and HO(CH2)2Br in C5H5N via the Br compound, m. 126-7%, and refluxing the latter with NaI in MeCN. The mechanisms are discussed. The new (OCMe2CMe2OCH)BF4 m. 110-12° and (Me2NCHOEt)SbCl6 m. 156-8°.

Annalen der Chemie, Justus Liebigs published new progress about Anions. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts