Tag: M.W=150-200

Parekh, Hansa published the artcilePreparation and resolution of (+-)-p-(α-cyanoarylamino)benzoic acid, Synthetic Route of 13312-84-0, the publication is Indian Journal of Chemistry (1973), 11(5), 501-3, database is CAplus.

α-Amino nitriles (±)-RCH(CN)NHC6H4COOH-p [(±)I:R = Ph, o-ClC6H4, p-MeOC6H4] were prepared by condensing an aldehyde cyanhydrin with p-aminobenzoic acid. The resolution of (±)(I) into optical isomers was accomplished through fractional crystallization of the brucine salts to give the resp. (-)-nitriles. With (±)-I (R = p-MeOC6H4), the (+)-nitrile was also obtained. The introduction of Cl in the Ph nucleus at the ortho-position enhanced the optical activity, while the MeO group at the paraposition decreased the optical activity.

Indian Journal of Chemistry published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Synthetic Route of 13312-84-0.

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

Frias, Maria published the artcileAsymmetric Synthesis of Rauhut-Currier type Products by a Regioselective Mukaiyama Reaction under Bifunctional Catalysis, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Journal of the American Chemical Society (2017), 139(2), 672-679, database is CAplus and MEDLINE.

The reactivity and the regioselective functionalization of silyl-diene enol ethers under a bifunctional organocatalyst provokes a dramatic change in the regioselectivity, from the 1,5- to the 1,3-functionalization. This variation makes possible the 1,3-addition of silyl-dienol ethers to nitroalkenes, giving access to the synthesis of tri- and tetrasubstituted double bonds in Rauhut-Currier type products. The process takes place under smooth conditions, nonanionic conditions, and with a high enantiomeric excess. A rational mechanistic pathway is presented based on DFT and mechanistic experiments

Journal of the American Chemical Society 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, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Smyth, Lynette A. published the artcileSynthesis and reactivity of 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones: development of a novel kinase-focussed library, HPLC of Formula: 57663-05-5, the publication is Tetrahedron (2010), 66(15), 2843-2854, database is CAplus.

3-Amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones represent a potentially attractive heteroaromatic scaffold for drug-discovery chem. In particular, the arrangement of hydrogen bond donor and acceptor groups in the bicyclic core can fulfil the requirements for ATP competitive binding to kinase enzymes. Efficient and regioselective routes from simple starting materials to novel functionalized 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones and related 3-amino-2H-pyrazolo[4,3-c]pyridines were explored and adapted for parallel synthesis, resulting in a library of compounds suitable for screening against kinases and other cancer drug targets. Methods for substituent variation at five distinct positions around the bicyclic core were devised to generate sets of compounds containing two- or three-point diversity.

Tetrahedron published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C14H31NO2, HPLC of Formula: 57663-05-5.

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

Campbell, Neil published the artcilePreparation of the halophenylacetic acids, Quality Control of 13312-84-0, the publication is Journal of the Chemical Society (1948), 1251-5, database is CAplus.

Gränacher’s synthesis (C.A. 16, 3898; 17, 2424) has been applied to the preparation of XC₆H₄CH₂CO₂H; the method depends on a satisfactory preparation of rhodanine (I), which is discussed. The yield of I depends upon the yield of H₂NCSSNH₄ (II) in the 1st stage of the reaction; the yield of II, as compared with that of CS(SNH₄)₂ (III), is a function of the NH₃ concentration which, in turn, is dependent on the temperature The more concentrated the NH₃ solution, the greater is the yield of III; the best yield of II is obtained at 10-15°; the yield of I from II is 44%. When the temperature is kept below 0%, III is the main product. Methods of distinguishing between II and III are given. Mol. quantities of aldehyde and I in AcOH (5 cc. per g. aldehyde), refluxed 0.5 h. with fused AcONa (twice the weight of I), give the following benzylidenerhodanines (IV): ο-Cl, pale yellow, m. 192°, 97% (Andreasch, C.A. 22, 3410, gives 169°); m-Cl, pale yellow, m. 233°, 93%; p-Cl, yellow, m. 231-2°, 93%; ο-Br, orange, m. 183.5°, 80%; m-Br, yellow, m. 238°, 90%; p-Br, yellow, m. 237-8°, 84%. IV were transformed into β-phenyl-α-thiopyruvic acids (V) by heating with 8 cc. 8% NaOH (per g. IV) at 50-5° until a clear or nearly clear solution resulted, cooling in an ice-salt bath, and acidifying rapidly with 3 N HCl; the crude acid in cold EtOH is precipitated with 1-2 volumes cold H₂O and recrystallized from MeOH, petr. ether, etc.; however, the crude acids were used in the next step. ο-Cl, m. 134-5°, 72% (A. gives 119-20°); m-Cl, straw-colored, m. 134°, 84%; p-Cl, yellow, m. 169-71°, 84% [a byproduct is probably α,α’-dithiobis(m-chlorocinnamic acid), yellow, m. 221-2°]; ο-Br, lemon-yellow, m. 142-3°, 70%; m-Br, pale yellow, m. 133-4°, 81%; p-Br, m. 165-80°, 75% (could not be purified further). α-Isonitroso-β-(halophenyl)propionic acids (VI) were prepared from V by refluxing (about 0.5 h.) in alc. containing 3 mols. NH₂OH (until H₂S evolution ceases); the crude acid is precipitated from dilute NaOH solution with concentrated HCl. ο-Cl, m. 156°, 83%; m-Cl, m. 149° (decomposition), 100%; p-Cl, m. 170° (decomposition) (1 sample m. 182°), 100%; ο-Br, m. 150° (decomposition), 100%; m-Br, m. 151°, 93%; p-Br, m. 173°, 85% (yields are of crude products). VI, refluxed 10 min. with Ac₂O (4 cc. per g. VI), the Ac₂O removed in vacuo, and the residue extracted with ether, give the (halophenyl)acetonitriles (VII): ο-Cl, b₁₁ 123-5°, 64%; m-Cl, b₁₀ 134-6°, 55%; p-Cl, b₁₂ 137-9°, m. 31-2°, 80%; ο-Br, b₁₃, 140-1°, 88%; m-Br, b₁₀ 145-7°, m. 27-8°, 70%; p-Br, b_10-12 152-6°, m. 48°, 72%. The over-all yields of the VII from the aldehydes were: ο-, m-, and p-Cl, 57, 47, 62%; ο-, m-, and p-Br, 49, 44, 38%; further losses, sometimes considerable, occur in the next step. VII were hydrolyzed by boiling with 60% H₂SO₄ or, preferably, with 20% EtOH-KOH, giving RC₆H₄CH₂CO₂H (R given): ο-Cl, m. 93-5° (p-nitrobenzyl ester, m. 70-1°); m-Cl, m. 77° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 138°); p-Cl, m. 104-6° (p-nitrobenzyl ester, m. 117°); ο-Br, m. 104-5° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 183-4°; anilide, m. 153-4°); m-Br, m. 102-3° (p-nitrobenzyl ester, m. 75-6°; p-toluidide, m. 135°); p-Br, m. 113-15° (p-nitrobenzyl ester, m. 128-9°; anilide, m. 174-6°; p-toluidide, m. 203°). The results show that this method leaves much to be desired. The crystalline compound from 20 g. p-BrC₆H₄CHO, 80 cc. NaHSO₃, and 5 cc. EtOH, stirred 2 h. with 10 g. KCN in 20 cc. H₂O, gives 12.5 g. p-bromomandelonitrile, m. 78-9°; 11 g. and 46 cc. HI (d. 1.94), refluxed 1 h. give 1.5 g. p-BrC₆H₄CH₂CO₂H; an unknown compound, m. 126-7°, is a byproduct. ο-ClC₆H₄CHO, through ο-ClC₆H₄CH(OH)CN, yields the benzoate (no properties given); refluxing with Pt black in tetralin did not give ο-ClC₆H₄CH₂CN. p-MeOC₆H₄CH₂CN was obtained in 39% yield (yield of intermediate benzoate 74 and 92% in 2 experiments). Other methods were tried without much success. A mixture of ο- and p-BrC₆H₄CH₂CO₂H could not be separated by fractional distillation of the acid chlorides or Et esters; chromatog. separation of the anilides, p-toluidides, and 2-naphthalides was only partially successful (they fluoresce in C₆H₆ but not on the Al₂O₃ column). α-(ο-Bromophenyl)aceto-2-naphthalide, m. 188-9°; p-isomer, m. 203-4°. α-Phenylaceto-2-naphthalide m. 162-3°. In the preparation of the naphthalides by heating the acids with 2-C₁₀H₇NH₂, (2-C₁₀H₇)₂NH is obtained, the catalyst presumably being the halo acid. 2-C₁₀H₇NH₂ and PhNH₂ give 2-C₁₀H₇NHPh, and p-MeC₆H₄NH₂ gives 2-C₁₀H₇NHC₆H₄Me-p, but ο- or m-ClC₆H₄NH₂ gives only (2-C₁₀H₇)₂NH. 2-C₁₀H₇NH₂ and its derivatives are more strongly adsorbed than the corresponding 1-derivatives

Journal of the Chemical Society published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Quality Control of 13312-84-0.

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

Henze, Henry R. published the artcileHydantoins containing a tetrahydropyranyl substituent, Computed Properties of 30431-99-3, the publication is Journal of the American Chemical Society (1942), 1672-4, database is CAplus.

Refluxing a mixture of 155 g. NCCH₂CO₂Et and 97 g. (ClCH₂CH₂)₂O with 31.5 g. of Na in 450 cc. EtOH for 3 h. gives 31% of the Et ester, b₁₆ 135°, n_D²⁰ 1.4539, d₄²⁰ 1.1109, γ²⁰ 37.4, of 4-cyanotetrahydro-4-pyrancarboxylic acid; heating the acid at 180-200° gives 90% of tetrahydro-4-pyrancarbonitrile (I), b₁₀ 82-3°, n_D²⁰ 1.4521, d₄²⁰ 1.0343, γ²⁰ 40.7. 4-Acyltetrahydropyrans, RCOCH(CH₂.CH₂)₂O, were prepared by addition of a mol. proportion of I in absolute ether to 1.2-2 M proportions of the Grignard reagent (R is given): Me, b₁₄₄ 205-7°, n_D²⁰ 1.4530, d₄²⁰ 1.0243, γ²⁰ 35.8, MR 33.98, 53% yield (semicarbazone, m. 178° (all m. ps. corrected)); Et, b₂₀ 101°, n 1.4541, d. 1.0016, γ 37.2, MR, 38.60, 72% (semicarbazone, m. 151°); Pr, b₅ 85-8°, n 1.4545, d. 0.9828, 57% (semicarbazone, m. 145-6°); Bu, b₅ 100°, n 1.4551, d. 0.9700, 67% (semicarbazone, m. 180°; 2,4-dinitrophenylhydrazone, m. 99°); iso-Bu, b₆ 90-2°, n 1.4545, d. 0.9648, γ 33.2, MR 47.83, 69% (semicarbazone, m. 187-8°; 2,4-dinitrophenylhydrazone, m. 122°); Am, b₅ 106-7°, n 1.4573, d. 0.9589, γ 33.3, MR 52.45, 64% (semicarbazone, m. 117°; 2,4-dinitrophenylhydrazone, m. 89-90°); iso-Am, b₇ 116-17°, n 1.4567, d. 0.9562, γ 32.9, MR 52.45, 65% (semicarbazone, m. 158-9°; 2,4-dinitrophenylhydrazone, m. 134-5°); hexyl, b₆ 134-5°, n 1.4569, d. 0.9446, MR 57.07, 61% (semicarbazone, m. 161°); cyclohexyl, b₅ 142°, n 1.4839, d. 1.0262, MR 54.87, 46% (semicarbazone, m. 213-14°); Ph, m. 57-8°, 67%. The ketone with 1.8 molar equivalents of KCN and 3.6 molar equivalents of (NH₄)₂CO₃ in about 150 cc. 50% EtOH heated 12 h. at 58-60° gives 5-substituted 5-(tetrahydro-4-pyranyl)hydantoins, HN.CO.NH.CO.CRCH(CH₂.CH₂)₂O (R given): Me, m. 250°, 51%; Et, m. 246°, 70%; Pr, m. 223°, 66%; Bu, m. 195°, 49%; iso-Bu, m. 222°, 53%; Am, m. 171-2°, 79%; iso-Am, m. 195-6°, 68%; hexyl, m. 169°, 48%; cyclohexyl, m. 304-6°, 65%; Ph, m. 253°, 72%. The iso-Am and Ph derivatives exhibit mild anticonvulsant activity and are devoid of any hypnotic action.

Journal of the American Chemical Society published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Computed Properties of 30431-99-3.

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

Zhao, Tong published the artcileDiscovery of novel indolylarylsulfones as potent HIV-1 NNRTIs via structure-guided scaffold morphing, HPLC of Formula: 612-13-5, the publication is European Journal of Medicinal Chemistry (2019), 111619, database is CAplus and MEDLINE.

For more in-depth exploration of the chem. space around the entrance channel of HIV-1 reverse transcriptase (RT), a series of novel indolylarylsulfones (IASs) bearing different chiral N-substituted pyrrolidines (R/S)-I [R¹ = methanesulfonyl, pyridin-3-ylmethyl, (2-fluorophenyl)methyl, (4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl, etc.], azetidines II or substituted sulfonamide groups III [R² = 2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)ethyl, ethanesulfonyl, cyclopropanesulfonyl, etc.] at indole-2-carboxamide were designed and synthesized as potent HIV NNRTIs by structure-guided scaffold morphing approach. All the IASs exhibited moderate to excellent potency against wild-type HIV-1 with EC₅₀values ranging from 0.0043 μM to 4.42 μM. Notably, compound (R)-I (R¹ = methanesulfonyl) (EC₅₀ = 4.7 nM, SI = 5183) and (S)-I (R¹ = methanesulfonyl) (EC₅₀ = 4.3 nM, SI = 7083) were identified as the most potent compounds, which were more active than nevirapine, lamivudine and efavirenz, and also reached the same order of etravirine. Furthermore, some compounds maintained excellent activity against various single HIV-1 mutants (L100I, K103 N, E138K, Y181C) as well as one double mutant (F227L/V106A) with EC₅₀ values in low-micromolar concentration ranges. Notably, II (R² = carbamoylmethyl) displayed outstanding potency against F227L/V106A (EC50 = 0.094 μM), and also showed exceptional activity against E138K (EC₅₀ = 0.014 μM), L100I (EC₅₀ = 0.011 μM) and K103 N (EC₅₀ = 0.025 μM). Addnl., most compounds showed markedly reduced cytotoxicity (CC₅₀) compared to lead compounds, especially II [R² = (2-cyanophenyl)methyl] (CC₅₀ >234.91 μM, SI >18727) and II (R² = methanesulfonyl) (CC₅₀ >252.49 μM, SI >15152). Preliminary SARs and mol. modeling studies were also discussed in detail, which may provide valuable insights for further optimization.

European Journal of Medicinal Chemistry published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C10H9NO, HPLC of Formula: 612-13-5.

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

Guo, Shuhui published the artcileTetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron Letters (2017), 58(30), 2881-2884, database is CAplus.

Tetraarylphosphonium inner-salts (TAPIS) were designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst was successfully applied in Michael addition, cyanation and trifluoromethylation reactions.

Tetrahedron 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, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Tang, Ren-Jin published the artcileFriedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is RSC Advances (2018), 8(19), 10314-10317, database is CAplus and MEDLINE.

An effective and clean Friedel-Crafts alkylation of indoles and electron-rich arenes with β-nitroalkenes in hexafluoroisopropanol is reported. The desired products were formed rapidly in excellent yields under mild conditions without the need for any addnl. catalysts or reagents. Further, this methodol. could be applied to one-pot synthesis of biol. active tryptamine derivatives

RSC Advances 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 C6H12Br2, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Sosic, Izidor published the artcileDiscovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B, HPLC of Formula: 612-13-5, the publication is European Journal of Medicinal Chemistry (2011), 46(9), 4648-4656, database is CAplus and MEDLINE.

Cathepsin B is a lysosomal cysteine protease that has various physiol. and pathophysiol. functions. We present here the discovery of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B, starting from screening of a library of variously 2,4,6-trisubstituted 1,3,5-triazines and 1,3,5-triazin-2(1H)-ones on three different human cathepsins. The synthesis and enzymic evaluation of a focused library of new 1,3,5-triazin-2(1H)-ones, e.g. I [R – o-OMe, m-F, p-NO₂, etc.], is also described. The detailed kinetics analyses have shown that these compounds can act as reversible, partial mixed-type inhibitors of cathepsin B, with K_i and K_i‘ values in the low micromolar range. The inhibitory activities of selected compounds were also assessed against two related cysteine proteases, cathepsin H and cathepsin L, to estimate their selectivity; these compounds have a selective profile for catB and catL over catH.

European Journal of Medicinal Chemistry published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C9H22OSi, HPLC of Formula: 612-13-5.

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

Gupta, Dinesh published the artcileCu (II)-β-CD as Water-Loving Catalyst for One-Pot Synthesis of Triazoles and Biofuels Intermediate at Room Temperature without Any Other Additive, Name: 2-(Chloromethyl)benzonitrile, the publication is ChemistrySelect (2017), 2(10), 2997-3008, database is CAplus.

The applications of Cu(II)-β-CD as water soluble green catalyst for the one-pot conversion benzyl halide to benzyl azide and 1,2,3-trizoles at room temperature and very short reaction time (15-70 min) was presented. Products were separated without any workup, simple by filtration, with >99 % selectivity and purity. As-synthesized material was characterized by, HR-TEM, XPS, FESEM, FT-IR, TGA and XRD to understand its structural properties as well as attachment of copper by host-guest interaction. This catalyst also showed effectiveness for the condensed ketone and aldehydes moiety, which produced biofuels intermediate. The recyclability of this catalytic system was tested up to five cycles and only a very slight loss of catalytic activity was detected.

ChemistrySelect published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

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