Tag: M.W=150-200

Xiao, Jing published the artcilePhosphonic acid mediated practical dehalogenation and benzylation with benzyl halides, Related Products of chlorides-buliding-blocks, the publication is RSC Advances (2019), 9(39), 22343-22347, database is CAplus and MEDLINE.

For the first time, by using H₃PO₃/I₂ system, various benzyl chlorides and bromides RCH₂X (R = C₆H₅, 4-O₂NC₆H₄, 1-naphthyl, etc.; X = Cl, Br) were dehalogenated successfully. In the presence of H₃PO₃, benzyl halides underwent electrophilic substitution reactions with electron-rich arenes, leading to a broad range of diarylmethanes RCH₂R¹ (R¹ = C₆H₅, 2,4,6-(CH₃)₃C₆H₂, 4-CH₃OC₆H₄, etc.) in good yields. These transformations feature green, cheap reducing reagents and metal-free conditions.

RSC Advances published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C14H26O2, Related Products of chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Ansideri, Francesco published the artcileStructural Optimization of a Pyridinylimidazole Scaffold: Shifting the Selectivity from p38α Mitogen-Activated Protein Kinase to c-Jun N-Terminal Kinase 3, Computed Properties of 6313-54-8, the publication is ACS Omega (2018), 3(7), 7809-7831, database is CAplus and MEDLINE.

Starting from known p38α mitogen-activated protein kinase (MAPK) inhibitors, a series of inhibitors of the c-Jun N-terminal kinase (JNK) 3 was obtained. Altering the substitution pattern of the pyridinylimidazole scaffold proved to be effective in shifting the inhibitory activity from the original target p38α MAPK to the closely related JNK3. In particular, a significant improvement for JNK3 selectivity could be achieved by addressing the hydrophobic region I with a small Me group. Furthermore, addnl. structural modifications permitted to explore structure-activity relationships. The most potent inhibitor 4-(4-methyl-2-(methylthio)-1H-imidazol-5-yl)-N-(4-morpholinophenyl)pyridin-2-amine showed an IC₅₀ value for the JNK3 in the low triple digit nanomolar range and its binding mode was confirmed by x-ray crystallog.

ACS Omega published new progress about 6313-54-8. 6313-54-8 belongs to chlorides-buliding-blocks, auxiliary class Pyridine,Chloride,Carboxylic acid, name is 2-Chloroisonicotinic acid, and the molecular formula is C6H4ClNO2, Computed Properties of 6313-54-8.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Farquharson, Muriel E. published the artcileThe effects of some derivatives of γ-aminobutyric acid on the slowly adapting stretch receptor of Astacus fluviatilis, Product Details of C7H16ClNO2, the publication is Journal of Medicinal & Pharmaceutical Chemistry (1961), 31-40, database is CAplus and MEDLINE.

γ-Aminobutyric acid (I) and some N-substituted amide and ester derivs, of the acid were studied for changes effected in the rate of impulses set up in response to constant stretching of the crayfish stretch receptor. Tests showed that γ-substitution increased the frequency of the impulse, I and two butyramides decreased the frequency of the impulse, and simultaneous substitution of both terminal groups of I had no noticeable effect on the impulse frequency. γ-Piperidinobutyronitrile (22.7 g.) was dissolved in 20 ml. MeOH, 48 ml. methanolic HCl added slowly with cooling, the mixture allowed to stand 1.25 hrs., refluxed 0.75 hr., cooled, the solid dissolved in a minimum of H₂O, the mixture made alk. with NH₃, extracted twice with 50 ml. Et₂O and twice with 40 ml. CHCl₃, the solvent removed, and the residue distilled in vacuo to give 21.5 g. Me γ-piperidinobutyrate (II), b_1-2 824°. The HCl salt, m. 146-8°, was made by dissolving II in iso-Pr₂O, neutralizing with HCl in iso-PrCl, washing the solid with Et₂O, and recrystallizing from EtOH-Et₂O. II (10 g.) and 50 ml. 0.880N NH₃ warmed on a steam bath 8 hrs., the mixture evaporated to dryness in vacuo, and the residue triturated with Me₂CO and recrystd, from dry Me₂ CO gave γ-piperidinobutyramide (III), m. 70-2°; III.HCl m. 190-2 °. Et γ-aminobutyrate-HCl (6.1 g.) and 25 ml. 0.880N NH₃ shaken 3 hrs. at room temperature in a closed vessel, the mixture evaporated to dryness in vacuo, the residue dissolved in iso-PrOH, filtered through Kieselguhr, dry HCl in iso-PrOH added to slight excess, and the solid recrystallized 3 times from iso-PrOH-Et₂O gave 0.68 g. γ-aminobutyramide-HCl, m. 126-9°. Prepared by the same method was γ-morpholinobutyric acid-HCl, m. 131-3°. Me γ-chlorobutyrate (8.2 g.) dissolved in 20 ml. dry Me₂CO, 10 g. NaI in 50 ml. Me₂CO added at room temperature with stirring, the mixture refluxed 1.5 hrs. and filtered, the solvent removed in vacuo, the residue taken up in 20 ml. MeOH, 120 ml. 33% MeNH₂ in MeOH added, the mixture refluxed 24 hrs. (dry ice trap), the quaternary iodide precipitated by addition of excess dry Et₂O, an aqueous solution of this iodide stirred 4 hrs. at room temperature with excess Ag₂O, filtered, evaporated to dryness in vacuo, the residue dissolved in 10 ml. MeOH, acidified with HCl in isoPr₂O, a small amount of dry Et₂O added to complete precipitation, the solid washed with dry Et₂O, and the product crystallized twice from absolute EtOH gave 2.2 g. γ-butyrobetaine-HCl, m. 21214°. γ-Chlorobutyric acid dissolved in 30 ml. C₆H₆, 30 ml. SOCl₂ added dropwise with stirring during 30 min., the mixture stirred an addnl. 2 hrs., allowed to stand overnight at room temperature, the excess SOCl₂ removed as an azeotrope with C₆H₆, and the residue distilled in vacuo gave the acid chloride (IIIa), b_1.5 40-2°. IIIa (22 g.) dissolved in 100 ml. dry Me₂CO, 26 g. piperidine in 100 ml. Me₂CO added dropwise with stirring and cooling, the solid filtered, the intermediate γ-chlorobutyrylpiperidine treated immediately with 27 g. NaI, the mixture allowed to stand at room temperature 2 hrs., filtered, 13 g. piperidine added, the mixture refluxed 11 hrs., cooled, Et₂O added in excess to precipitate the piperidine HCl salt, the solid filtered, and the filtrate distilled and then fractionated in vacuo gave γ-piperidinobutyrylpiperidine (IV), b_1.5 162°, n²¹_D 1.4999; IV.HCl m. 177-8°. Also prepared was Et γ-dimethylaminobutyrate methiodide, m. 151-2°.

Journal of Medicinal & Pharmaceutical Chemistry published new progress about 6249-56-5. 6249-56-5 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst,Inhibitor,Natural product, name is 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride, and the molecular formula is C7H16ClNO2, Product Details of C7H16ClNO2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Lightowler, J. E. published the artcileAnalogs of γ-aminobutyric acid [as anticonvulsant agents], Synthetic Route of 6249-56-5, the publication is Archives Internationales de Pharmacodynamie et de Therapie (1963), 145(1/2), 233-42, database is CAplus.

Owing to the role of p-aminobutyric acid (I) in the central nervous system, experiments were made on the action of various I derivatives and other compounds against convulsive agents such as strychnine (II), leptazol (III), and Megimide (IV). The compounds were usually injected into the tail veins of mice. The compounds tested (full chem. names given) for anticonvulsant activity and for 24-hr. L.D.₅₀ values in mice were mostly compounds of the DF series. In some experiments the anticonvulsant effects were determined by oral administration. None of the L.D. series of compounds had any strongly antagonistic action against II, III, or IV, although in certain cases limited antagonistic effects were obtained. I itself gave no protection against II convulsions. Troxidone (V) was active against both III and IV, which may be of interest since V is chemically related to DF 666 (2-pyrroli-dinone) which has been suggested as a biol. precursor of I. Except for I, the compounds showed little activity against histamine or acetylcholine applied to the isolated guinea pig ileum. I alone had a direct effect on the isolated ileum. Following previous stimulation, the application of I caused an extremely rapid contraction and relaxation. Up to about 100 mg./ml., this effect increased with the concentration of I, but could only be repeated after a considerable time had elapsed between subsequent applications. 19 references.

Archives Internationales de Pharmacodynamie et de Therapie published new progress about 6249-56-5. 6249-56-5 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst,Inhibitor,Natural product, name is 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride, and the molecular formula is C7H16ClNO2, Synthetic Route of 6249-56-5.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chen, Tiffany Q. published the artcileA Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides, Application of 1-(Chloromethyl)-4-(trifluoromethyl)benzene, the publication is Angewandte Chemie, International Edition (2019), 58(41), 14584-14588, database is CAplus and MEDLINE.

Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of aryl bromide coupling partners, is predicated upon a halogen atom abstraction/nickel radical-capture mechanism that is generically successful across an extensive range of carbonyl substrates. The construction and use of arylacetic acid products have further enabled two-step protocols for the delivery of valuable building blocks for medicinal chem., such as aryldifluoromethyl and diarylmethane motifs.

Angewandte Chemie, International Edition published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C8H6ClF3, Application of 1-(Chloromethyl)-4-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Josa-Cullere, Laia published the artcileA Phenotypic Screen Identifies a Compound Series That Induces Differentiation of Acute Myeloid Leukemia Cells In Vitro and Shows Antitumor Effects In Vivo, Synthetic Route of 209919-30-2, the publication is Journal of Medicinal Chemistry (2021), 64(21), 15608-15628, database is CAplus and MEDLINE.

Induction of differentiation is a promising therapeutic strategy against acute myeloid leukemia. However, current differentiation therapies are effective only to specific patient populations. To identify novel differentiation agents with wider efficacy, authors developed a phenotypic high-throughput screen with a range of genetically diverse cell lines. From the resulting hits, one chem. scaffold was optimized in terms of activity and physicochem. properties to yield OXS007417 I, a proof-of-concept tool compound, which was also able to decrease tumor volume in a murine in vivo xenograft model.

Journal of Medicinal Chemistry published new progress about 209919-30-2. 209919-30-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-Chloro-2-methylphenylboronic acid, and the molecular formula is C7H8BClO2, Synthetic Route of 209919-30-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Djud, Mateja published the artcileSynthesis of monosubstituted thioureas by vapour digestion and mechanochemical amination of thiocarbamoyl benzotriazoles, Recommanded Product: 1-(4-Chlorophenyl)thiourea, the publication is Green Chemistry (2016), 18(9), 2666-2674, database is CAplus.

Thiocarbamoyl benzotriazoles, as safe and easy-to-handle isothiocyanate equivalent, were quant. converted to N-monosubstituted thioureas by vapor digestion synthesis under an ammonia atm. This simple, but timely process provided a synthetic platform that enabled the “slow” amination reaction to be successfully transformed into a rapid one aided by mechanochem. milling. The ammonium chloride/sodium carbonate equimolar mixture allowed in situ formation of ammonia under ball-milling conditions. This novel and green approach yielded aromatic and aliphatic primary thioureas in near-quant. isolated yields with workup entirely based on using only water. In addition, the mol. and crystal structures of selected polyaromatic primary thioureas were determined from the synchrotron powder diffraction data.

Green Chemistry published new progress about 3696-23-9. 3696-23-9 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Thiourea,Amine,Benzene,Amide, name is 1-(4-Chlorophenyl)thiourea, and the molecular formula is C7H7ClN2S, Recommanded Product: 1-(4-Chlorophenyl)thiourea.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Agrawal, V. L. published the artcileSynthesis and properties of 3-substituted benzothiazolyl 1-phenyl amino methanamides with Cu(II) complex compound, Product Details of C7H7ClN2S, the publication is International Journal of Chemical Sciences (2014), 12(4), 1677-1680, database is CAplus.

Several complexes of Cu(II) are formed by refluxing purified Cu palmitate with 3-substituted benzothiazolyl 1-Ph amino methanamide, RC₇H₄NS-NHC(O)NHPh (R = H, 4-Me, 6-Me, 4-Cl, 6-NO₂), in the ratio 1:1.7 using EtOH as a solvent for four hrs. Resultant solution was filtered hot and complexes were recrystallized using petroleum ether solvent. Granular solid complexes of different colors like light blue, green gray and blackish were obtained in sufficient yield.

International Journal of Chemical Sciences published new progress about 3696-23-9. 3696-23-9 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Thiourea,Amine,Benzene,Amide, name is 1-(4-Chlorophenyl)thiourea, and the molecular formula is C7H7ClN2S, Product Details of C7H7ClN2S.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Golzadeh, Robab published the artcileGreen synthesis of methadone in eutectic solvent, Name: 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, the publication is Main Group Chemistry (2021), 20(4), 463-474, database is CAplus.

Synthesis of di-Ph acetonitrile with 1-dimethylamino-2-chloropropane by a eutectic’s solvent was described. In addition, methadone I was synthesized from the reaction of 2,2-diphenyl-4-dimethylaminovaleronitrile with Et magnesium bromide in the presence of solvent eutectic, which was in optimal and environmentally compatible conditions and by principles of green chem.

Main Group Chemistry published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Name: 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Cross, R. Matthew published the artcileOptimization of 1,2,3,4-Tetrahydroacridin-9(10H)-ones as Antimalarials Utilizing Structure-Activity and Structure-Property Relationships, Synthetic Route of 209919-30-2, the publication is Journal of Medicinal Chemistry (2011), 54(13), 4399-4426, database is CAplus and MEDLINE.

Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine in the 1970s and analogs thereof such as WR 243251 in the 1990s. These compounds failed just prior to clin. development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochem. liabilities of the THA scaffold. Several potent compounds (EC₅₀ < 100 nM) were identified to be active against the clin. relevant isolates W2 and TM90-C2B while possessing good physicochem. properties and little to no cross-resistance.

Journal of Medicinal Chemistry published new progress about 209919-30-2. 209919-30-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-Chloro-2-methylphenylboronic acid, and the molecular formula is C7H8BClO2, Synthetic Route of 209919-30-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics