indole-building-block | - Page 80 of 1434

Kaila, Neelu et al. published their research in Journal of Medicinal Chemistry in 2007 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application of 150560-58-0

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists was written by Kaila, Neelu;Janz, Kristin;DeBernardo, Silvano;Bedard, Patricia W.;Camphausen, Raymond T.;Tam, Steve;Tsao, Desiree H. H.;Keith, James C. Jr.;Nickerson-Nutter, Cheryl;Shilling, Adam;Young-Sciame, Ruth;Wang, Qin. And the article was included in Journal of Medicinal Chemistry in 2007.Application of 150560-58-0 This article mentions the following:

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewis^x (sLe^x) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small mol. P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chem. library identified the quinoline salicylic acid class of compounds as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLe^x. Through iterative medicinal chem., it was identified analogs with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound , I, was efficacious in the rat AIA model of rheumatoid arthritis. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Application of 150560-58-0).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Kutuk, Halil et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 2011 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C14H9NO2S

Microwave-Assisted Synthesis of Disulfides was written by Kutuk, Halil;Turkoz, Nalan. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2011.Synthetic Route of C14H9NO2S This article mentions the following:

A new microwave-assisted synthesis methodol. for the preparation of substituted disulfide derivatives is presented. 4-Substituted sulfenimides were reacted with 4-substituted thiols under neat (to right doughy consistency) conditions in chloroform, with both microwave heating and conventional methods. The resulting 4-substituted disulfide derivatives were obtained at higher yields and in shorter reaction times with microwave heating. Their chem. was confirmed by ¹H-NMR, ¹³C-NMR, IR, and elemental anal. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Synthetic Route of C14H9NO2S).

Hemenway, Jeffrey N. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2007 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.COA of Formula: C14H9NO2S

Preparation, characterization and in vivo conversion of new water-soluble sulfenamide prodrugs of carbamazepine was written by Hemenway, Jeffrey N.;Nti-Addae, Kwame;Guarino, Victor R.;Stella, Valentino J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.COA of Formula: C14H9NO2S This article mentions the following:

Improved synthetic methods were reported for the preparation of sulfenamide derivatives I [R = SPh, SCH₂CH(NH₂)CO₂Et, S(CH₂)₂NH₂] of carbamazepine (CBZ) I (R = H) for evaluation as prodrugs. These sulfenamide prodrugs were designed to rapidly release CBZ in vivo by cleavage of the sulfenamide bond by chem. reaction with glutathione and other sulfhydryl compounds Physicochem. characterization and in vivo conversion of the new prodrug I [R = S(CH₂)₂NH₂] of CBZ was evaluated to further establish the proof of concept of the sulfenamide prodrug approach. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

Adam, Rosa et al. published their research in Angewandte Chemie, International Edition in 2016 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application of 5388-42-1

Esters, Including Triglycerides, and Hydrogen as Feedstocks for the Ruthenium-Catalyzed Direct N-Alkylation of Amines was written by Adam, Rosa;Cabrero-Antonino, Jose R.;Junge, Kathrin;Jackstell, Ralf;Beller, Matthias. And the article was included in Angewandte Chemie, International Edition in 2016.Application of 5388-42-1 This article mentions the following:

Triglycerides are used for the direct N-alkylation of amines with mol. hydrogen for the first time. A broad range of interesting and industrially relevant secondary and tertiary amines are obtained in the presence of an in situ formed Ru/Triphos complex. Notably, plant oil can be efficiently applied in this single-step process. Moreover, a variety of other Me esters can be used as N-alkylation agents in the presence of hydrogen for the synthesis of more advanced building blocks. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).

Tao, Zhonglin et al. published their research in Journal of the American Chemical Society in 2018 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 14204-27-4

Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration was written by Tao, Zhonglin;Robb, Kevin A.;Panger, Jesse L.;Denmark, Scott E.. And the article was included in Journal of the American Chemical Society in 2018.SDS of cas: 14204-27-4 This article mentions the following:

A catalytic, enantioselective method for the preparation of chiral, non-racemic, alkylboronic esters bearing two vicinal stereogenic centers is described. The reaction proceeds via a 1,2-migration of a zwitterionic thiiranium-boronate complex to give exclusively anti carbosulfenylation products. A broad scope of aryl groups migrate with good yield and excellent enantioselectivity (up to 99:1 e.r.). Similarly, a range of di- and trisubstituted alkenylboronic esters are competent reaction partners. This method provides access to both secondary and tertiary chiral alkylboronic esters. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).

Stirling, C. J. M. et al. published their research in Journal of the Chemical Society in 1960 | CAS: 5388-42-1

Intramolecular reactions of amides. II. Cyclization of amides of 闂?bromocarboxylic acids was written by Stirling, C. J. M.. And the article was included in Journal of the Chemical Society in 1960.Reference of 5388-42-1 This article mentions the following:

C₆H₁₁NH₂ (45 g.) in 100 ml. Et₂O added to 缂?bromobutyryl chloride (from 38 g. acid) in 300 ml. Et₂O gave 38 g. 缂?bromo-N-cyclohexylbutyramide (I), m. 60闂? I heated at 100闂?gave 2-cyclohexyliminotetrahydrofuran H Br salt (II), m. 132闂? from which the base (III), b. 134闂?7 mm., n_D²⁰ 1.4945 (methiodide m. 187-8闂?, was obtained. III (2 g.) in 20 ml. 20% aqueous H₂SO₄ 16 hrs. at 100闂?gave 0.5 g. 缂?butyrolactone (IV), b. 97闂?18 mm., n_D²² 1.4350, and 1.0 g. C₆H₁₁NH₂. III (10 g.) with 2 g. LiAlH₄ gave 4.6 g. 4-cyclohexylaminobutanol, b. 153闂?9 mm., n₂₁_D 1.4830, m. 45.6闂? III with PhMgBr gave a product of unknown structure. I (3.5 g.) refluxed 24 hrs. in 10 ml. EtOH and 500 ml. Et₂O added yielded 0.77 g. C₆H₁₁NH₃Br. Evaporation of the filtrate gave 0.34 g. IV after distillation and 2.1 g. N-cyclohexyl-缂備礁澧介幆鍧県oxybutyramide (V), m. 68.5闂? I (5 g.) with 15 g. powd. KOH 3 min. at 100闂?gave 1.2 g. 1-cyclohexyl-2-pyrrolidone, b. 154闂?7 mm., n_D¹⁴ 1.5005. II (3 g.) refluxed 24 hrs. in 10 ml. EtOH gave 0.4 g. IV and 1.85 g. V. 缂?Ethoxybutyryl chloride (from 1.7 g. acid) with C₆H₁₁NH₂ gave 1.5 g. V. 缂?Bromobutyranilide (VI) resisted cyclization. Ethanolysis of 3 g. VI gave 100% IV. VI (7 g.) and 3.1 g. Et₃N refluxed 1 hr. in 25 ml. EtOH gave 3.3 g. 1-phenyl-2-pyrrolidone, b. 188/14 mm., m. 66-8闂? 缂?Bromo-N-butylbutyramide (25 g.) kept. 1.5 hrs. at 125闂?gave 2.4 g. 2-butyliminotetrahydrofuran (VII), b. 92闂?9 mm., n_D¹⁸ 1.4593. Hydrolysis of 0.9 g. VII in 20% H₂SO₄ 24 hrs. at 100闂?gave 0.2 g. IV and BuNH₂ (55 g. p-nitrobenzoyl derivative, m. 100-1闂?. VII (2.9 g.) with 1 g. LiAlH₄ gave 1.1 g. 4-butylaminobutanol, b. 132闂?10 mm., n_D²¹ 1.4508. N-Benzyl-缂?bromobutyramide, m. 58闂? could not be cyclized. 5-Bromo-N-cyclohexylvaleramide (VIII) (12 g.) heated 1 hr. at 100闂?and Et₂O added yielded 7 g. 2-cyclohexyliminotetrahydropyran HBr salt (IX), m. 108-9闂? IX (4.6 g.) in 20 ml. H₂O was added to 100 ml. saturated brine, 200 ml. Et₂O and 20 ml. 10% aqueous KOH added, then the base quickly extracted and distilled to give 1.9 g. 2-cyclohexyliminotetrahydropyran (X), b. 134闂?8 mm., n_D²¹ 1.4980. X (1.6 g.) with 0.5 g. LiAlH₄ gave 0.89 g. 5-cyclohexylaminopentanol, m. 74-5闂? Ethanolysis of 2 g. VIII gave 0.7 g. C₆H₁₁NH₃Br and 0.3 g. 闂?valerolactone (XI), b. 12 mm. IX (0.6 g.) with 10 ml. 20% H₂SO₄ 16 hrs. at 100闂?gave 0.05 g. XI and 98% C₆H₁₁NH₂. 5-Bromovaleranilide (3 g., m. 96-7闂? refluxed 3 hrs. in 10 ml. EtOH gave 1.27 g. PhNH₃Br and 0.5 g. XI. o-Bromomethylbenzoyl bromide (XIII) (23 g.) with 17 g. PhNH₂ in 300 ml. Et₂O gave 15 g. 2-bromomethylbenzanilide (XIII), m. 83闂? XIII fused at 130闂?gave 1,3-dihydro-1-phenyliminoisobenzofuran HBr salt (XIV), m. 164-5闂? XIV (14 g.) in H₂O basified with aqueous Na₂CO₃ gave 10 g. 1,3-dihydro-1-phenyliminoisofuran (XV), m. 99.5闂? XV (0.75 g.) in 20% H₂SO₄ 1.5 hrs. at 100闂?gave 0.40 g. phthalide (XVI) and 92% PhNH₂. XV (1 g.) 2 hrs. at 300闂?gave 0.7 g. N-phenylisoindolinone, m. 166-7闂? XV (3.5 g.) with 1 g. LiAlH₄ gave 2.7 g. 2-hydroxymethyl-N-phenylbenzylamine, b. 156闂?0.03 mm., m. 59-60闂? XII (21 g.) with 18 g. PhCH₂NH₂ in 250 ml. Et₂O gave 7 g. 1-benzylimino-1,3-dihydroisobenzofuran (XVII), m. 37-8闂? n_D²⁵ 1.6103 (methiodide, m. 143-4闂?. Hydrolysis of XVII with 20% H₂SO₄ gave 88% XVI and 97% PhCH₂NH₂. XVII.HBr (5 g.) refluxed 5 hrs. in 10 ml. EtOH gave 1.62 g. PhCH₂NH₃Br, m. 225闂? 1.13 g. XVI, and 0.5 g. N-benzyl-2-ethoxymethylbenzamide, m. 86.5闂? XVI (3 g.) and PhCH₂NH₂ heated 3 hrs. at 260闂?gave 3.2 g. 2-benzylisoindolinone, m. 90闂? Similarly, XVI and C₆H₁₁NH₂ gave 2-cyclohexylisoindolinone, m. 112-13闂? XII (10.5 g.) with 7.2 g. C₆H₁₁NH₂ in 150 ml. Et₂O gave 4 g. 1-cyclohexylimino-1,3-dihydrobenzofuran (XVIII), m. 79-80闂?(methiodide m. 202闂?. Hydrolysis of XVIII gave 92% XVI and 87% C₆H₁₁NH₂. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Li, Shunian et al. published their research in Organic Chemistry Frontiers in 2021 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). COA of Formula: C8H3F2NO2

Ni-Catalyzed asymmetric hetero-Diels-Alder reactions of conjugated vinyl azides: Synthesis of chiral azido polycycles was written by Li, Shunian;Lu, Haifeng;Xu, Zhenghu;Wei, Fang. And the article was included in Organic Chemistry Frontiers in 2021.COA of Formula: C8H3F2NO2 This article mentions the following:

The authors describe an efficient Ni(II)/Feng ligand-catalyzed asym. hetero-Diels-Alder reaction between conjugated vinyl azides RC(:CH₂)N₃ [R = 1-cyclohexenyl, 1-cyclopentenyl, C₆H₅CH:CH, C₆H₅C(:CH₂)] and carbonyl groups in compounds such as isatins I (R¹ = H, 5,6-F₂, 7-Br, 5-Me, etc.) and R²C(O)C(O)OR³ (R² = H, Ph, 4-MeOC₆H₄, 4-FC₆H₄, 4-MeC₆H₄, R³ = Me, Et). This method provides a platform for the synthesis of complicated chiral azido polycycles II (R⁴ = H, 10,11-F₂, 9-Br, 11-OCF₃, 11-Me, etc.) and III in high yields and excellent enantioselectivities. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0COA of Formula: C8H3F2NO2).

Wang, Tianlong et al. published their research in Tetrahedron in 2020 | CAS: 5388-42-1

Investigation towards the reductive amination of levulinic acid by B(C₆F₅)₃/hydrosilane system was written by Wang, Tianlong;Xu, Hai;He, Jianghua;Zhang, Yuetao. And the article was included in Tetrahedron in 2020.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The selective transformation of the renewable biomass resources into the highly value-added platform chems. is essentially important for sustainable chem. Here the authors report a simple and highly efficient strategy for the synthesis of N-heterocyclic compounds from the reductive amination of the bio-derived levulinic acid and a wide range of anilines by metal-free B(C₆F₅)₃/hydrosilane catalyst system. Through adjusting the amounts of hydrosilane, the authors can synthesize a series of pyrrolidones or pyrrolidines, resp. Isotope-labeled NMR experiments were conducted to investigate the possible reaction pathway. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

Liu, Ruixing et al. published their research in Organic Letters in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 6-Nitro-1H-indole

Activation Relay on Rhodium-Catalyzed C-H Aminomethylation in Cooperation with Photoredox Catalysis was written by Liu, Ruixing;Liu, Jiaxin;Wei, Yin;Shi, Min. And the article was included in Organic Letters in 2019.Name: 6-Nitro-1H-indole This article mentions the following:

A site selective C-H aminomethylation at indole’s C3 position was achieved by merging rhodium(III)-catalyzed C-H activation and photoredox catalysis in a one-pot manner. A study of the mechanistic insights rationalized the essence of the activation relay and the combination mode. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Prey, V. et al. published their research in Monatshefte fuer Chemie in 1960 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.SDS of cas: 5388-42-1

The rearrangement of 1-thiophthalide was written by Prey, V.;Kerres, B.;Berbalk, H.. And the article was included in Monatshefte fuer Chemie in 1960.SDS of cas: 5388-42-1 This article mentions the following:

The rearrangement of the title compound (I) in the presence of primary, secondary, and tertiary bases, with or without pressure, was studied and a reaction scheme was proposed, and through conductivity, heat of combustion, and infrared measurement, the important intermediate stages for tertiary bases were identified. Thus, 2 g. I and 5 g. PhNH₂ was heated in a sealed tube 3 hrs. at 190闂? and then about 0.1N HCl was added and a brown oil separated; this was crystallized from EtOH and then from H₂O to give 1.65 g. 2-thiophthalide (II), m. 59-60闂? Some similar representative experiments with I were (reagent, molar ratio of reagent to I, temperature, time, product, m. p., % yield given): PhNH₂, 1:5, 180闂? 1 hr., II, 60闂? quant.; PhNH₂, 1:25, 190闂? 2 hrs., N-phenylphthalimide (III), 168闂? 92; PhNH₂, 1:4 (sealed), room, 1 month, I, 116-17闂? 95; PhNH₂, 1:4 (open), room, 1 week, III, 168闂? -; MePhNH, 1:1, 190闂? 3 hrs., I, -, 100; Et₂PhN, 1:5, 190闂? 3 hrs., I, -, 100; o-ClC₆H₄NH₂, 1:5, 190闂? 3 hrs., N-(o-chlorophenyl)phthalimide, 206闂? 86; p-ClC₆H₄NH₂, 1:5, 190闂? 3 hrs., N-(p-chlorophenyl)phthalimide, 182-3闂? 96; o-toluidine, 1:5,190闂? 3 hrs., I,-, 100; BuNH₂, 1:4, 190闂? 3 hrs., o,o’-bis(butylaminomethyl)benzoyl sulfide (IV), 181-2闂? about 5; aqueous NH₃, -, 190闂? 3 hrs., diphthalyldiimide (V), 300闂? -; aqueous NH₃, -, 240闂? 3 hrs., II, -, 40; aqueous NH₃, -, reflux, 3 hrs., phthalide, 68-70闂? 50; pyridine, 1:5, about 100闂? 3 hrs., II,-, 100; quinoline, 1:5, 190闂? 3 hrs., II,-, 100; Et₃N, 1:1, 190闂? 4 hrs., II,-, 97. IV when heated with H₂O gave H₂S, and the filtrate from IV when treated with concentrated HCl gave II. A solution of 2.4 g. NaHS and 5 g. phthalide was heated 3 hrs. at 200闂?and treated with concentrated HCl to give 3.5 g. dibenzyl sulfide-o,o’ dicarboxylic acid, m. 230-3闂? dibutylamide m. 244-6闂? The EtOH filtrate from V was concentrated and the residue was purified with tetrahydrofuran and C to give 21.7% II, m. 54-9闂? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).