200-300 | - Page 6 of 43 - Indole Building Blocks

Fox, Sidney W. et al. published their research in Journal of the American Chemical Society in 1951 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid

Synthesis of 3-indoleacetic acids and 2-carboxy-3-indoleacetic acids with substituents in the benzene ring was written by Fox, Sidney W.;Bullock, Milon W.. And the article was included in Journal of the American Chemical Society in 1951.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Preceding abstract Cyclization of the corresponding succinaldehydic acid phenylhydrazones yielded the following 3-indoleacetic acid derivatives (m.p. and yield (%) given): 5-Cl, 158-9.5闂?(decomposition), 20; 7-Cl, 164-5闂? 13; 5,7-di-Cl 194-7闂?(decomposition), 9; 5-Me, 151-2闂? 31; 4-Cl, 185-7闂?(decomposition), 19; 6-Cl, 187-8闂?(decomposition), 26; 4- and 6-Cl eutectic mixture, 158-9闂?(decomposition), 16. 2,6-Cl(O₂N)C₆H₄Me (Uhle, C.A. 43, 4255d) yielded 4-chloroindole (I), b₁₃ 150闂? n_D²⁰ 1.6286, d₂₀²⁰ 1.259. I (8.0 g.), 4.3 g. 36% HCHO, 9.3 g. 25% Me₂NH, and 26 cc. AcOH allowed to stand at room temperature overnight, distilled in vacuo, 75 cc. water added, and the mixture filtered and made alk. with N NaOH yielded 8.4 g. 4-chlorogramine (II), m. 147-8.5闂?(150-1闂?when heated fairly rapidly) (from Me₂CO). Attempted conversion of II to 4-chloro-3-indoleacetic acid yielded a small amount of crude acid and an unidentified, higher-melting solid. 4,2-Cl-(O₂N)C₆H₃Me yielded 6-chloro-2-indolecarboxylic acid (III), m. 242-4闂?(decomposition) (from aqueous EtOH). III (8.8 g.) added to 60 cc. tech., anhydrous quinoline containing 5 g. CuCl at 150闂? the mixture heated 3 h. at 240闂?(bath temperature), cooled, triturated with Et₂O, shaken with water, the solid filtered off, washed with dilute HCl and Et₂O, the water-Et₂O mixture acidified with HCl, and the Et₂O distilled yielded 5 g. 6-chloroindole (IV), m. 83.6闂? EtMgI (35 cc. of a 0.033 M solution) added to 5 g. IV in 25 cc. Et₂O, the mixture stirred at ice-bath temperature 1 h., 2.8 g. ClCH₂CN in 25 cc. Et₂O added dropwise, the mixture stirred 30 min. at 0闂? refluxed 4 h., cooled, 3 cc. AcOH in 50 cc. water added, then 50 cc. C₆H₆, the mixture allowed to stand overnight, the aqueous layer extracted with C₆H₆ (solid discarded), the Et₂O-C₆H₆ layer distilled, the residue distilled at 160-80闂?0.2, the distillate refluxed 4 h. with 10 cc. MeOH and 20 cc. 20% aqueous KOH, filtered with C through diatomaceous earth, the filtrate extracted with Et₂O, and the aqueous layer acidified yielded 1.8 g. 6-chloro-3-indoleacetic acid. Cyclization of the 婵?ketoglutaric acid phenylhydrazones obtained as byproducts yielded the following 2-carboxy-3-indoleacetic acids (m.p. (decomposition), and yield (%) given): 7-Cl, 253闂? 31; 5-Me, 243闂? -; 7-Me, 228-9闂? 6; 5-Br, 247-8闂? 13. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

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

Hulpia, Fabian et al. published their research in European Journal of Medicinal Chemistry in 2018 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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.Name: 3-Bromo-4-chloro-7-azaindole

Synthesis of a 3′-C-ethynyl-闁?D-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides was written by Hulpia, Fabian;Noppen, Sam;Schols, Dominique;Andrei, Graciela;Snoeck, Robert;Liekens, Sandra;Vervaeke, Peter;Van Calenbergh, Serge. And the article was included in European Journal of Medicinal Chemistry in 2018.Name: 3-Bromo-4-chloro-7-azaindole This article mentions the following:

A focused nucleoside library was constructed around a 3′-C-ethynyl-D-ribofuranose sugar scaffold, which was coupled to variously modified purine nucleobases. The resulting nucleosides were probed for their ability to inhibit tumor cell proliferation, as well as for their activity against a panel of relevant human viruses. While C6-aryl substituted purine nucleosides were found to be weakly active, several C7-substituted 7-deazapurine nucleosides elicited potent antiproliferative activity. Their activity spectrum was evaluated in the NCI-60 tumor cell line panel indicating activity against several solid tumor derived cell lines. Analog I, equipped with a 7-deaza 7-chloro-6-amino-purin-9-yl base was evaluated in a metastatic breast tumor (MDA-MB-231-LM2) xenograft model. It inhibited both tumor growth and reduced the formation of lung metastases as revealed by BLI anal. The dideazanucleoside analog II showed interesting activity against hCMV. These results highlight the potential advantages of recombining known sugar and nucleobase motifs as a library design strategy to discover novel antiviral or antitumor agents. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Name: 3-Bromo-4-chloro-7-azaindole).

Lou, Qinxin et al. published their research in Advanced Synthesis & Catalysis in 2017 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Electric Literature of C8H6BrNO

Organocatalytic Enantioselective Synthesis of Dihydropyrano- indole Derivatives Bearing Trifluoromethylated All-Carbon- Substituted Stereocenters was written by Lou, Qinxin;Ding, Yuyang;Xu, Dengfeng;Liu, Guokai;Zhao, Junling. And the article was included in Advanced Synthesis & Catalysis in 2017.Electric Literature of C8H6BrNO This article mentions the following:

Malononitrile and isatin-derived trifluoromethylacrylates underwent a Michael addition/cyclization reaction, a process that was catalyzed efficiently by a bifunctional squaramide to afford a range of dihydropyranoindole derivatives bearing trifluoromethylated all-carbon-substituted stereocenters in high yields (up to 99%) with excellent enantioselectivity (up to 98% ee). This transformation was also examined with Et cyanoacetate as a nucleophile using a bifunctional thiourea as catalyst affording moderate yields (up to 79%) and high enantioselectivity (up to 98% ee). One of the products was used for the synthesis of a biol. interesting triazolopyrimidine derivative In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Electric Literature of C8H6BrNO).

Suwa, Satoshi et al. published their research in Chemical & Pharmaceutical Bulletin in 1999 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C14H9NO2S

AlCl₃-mediated aromatic phenylthiation with N-phenylthiophthalimide was written by Suwa, Satoshi;Sakamoto, Takeshi;Kikugawa, Yasuo. And the article was included in Chemical & Pharmaceutical Bulletin in 1999.Electric Literature of C14H9NO2S This article mentions the following:

N-Phenylthiophthalimide reacts with AlCl₃ or TiCl₄ in arenes to give phenylthiated arenes alone via a phenylsulfenium ion intermediate. MNDO MO calculations revealed that the pos. charge preferentially populates the sulfur atom rather than the Ph group in the phenylsulfenium ion. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).

Huang, Min-Lon et al. published their research in Hua Hseuh Hseuh Pao in 1961 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.COA of Formula: C9H5BrN2

Modified Wolff-Kishner method was written by Huang, Min-Lon;Chung, Tung-Shun;Ku, Tu-Shin;Chow, Wei-Zan. And the article was included in Hua Hseuh Hseuh Pao in 1961.COA of Formula: C9H5BrN2 This article mentions the following:

Successful usage of the Wolff-Kishner reduction was extended to many alkali-sensitive carbonyl compounds through the delayed addition of the alkali reagent. This modification afforded good yields of 1,2-diphenylethane (I) from benzil (II) and benzoin (III), PhCH₂CH₂CO₂H (IV) from PhCH₂COCO₂H (V), PhCH₂CH₂CH₂CO₂H (VI) from PhCOCH₂CH₂CO₂H (VII), and the normal reduction products from other 婵?oxo compounds A lower yield was obtained with furaldehyde (VIII). On the other hand, 闁?oxo compounds do not yield the normal reduction products, but, instead, cyclic N compounds (e.g., IX), while most 婵?闁?unsaturated ketones give rise to cyclopropane derivatives (e.g., X). Thus, 1.5 g. II, 15 ml. diethylene glycol (XI), and 6 ml. 85% hydrazine hydrate (XII) was refluxed 1 hr., the mixture cooled to room temperature, and 1.5 g. KOH was added. The mixture was refluxed 10-20 min. and distilled (to 190闂? liquid temperature) to remove water and excess XII. The residue was refluxed 3 hrs. at 195-200闂? cooled, and diluted with H₂O. The white precipitate formed was filtered off, washed, and dried in a desiccator to yield 1.2 g. I, m. 52-3闂?(EtOH). Similarly, 3 g. III, 20 ml. XI, 10 ml. 80% XII, followed by 2 g. KOH, gave 84.8% II. The unmodified Wolff-Kishner method, with the KOH added at the beginning of the reaction, yielded only 50.1% I. Similarly prepared were (product, physical constants, % yield, and starting material given): IV, m. 50-1闂? 76.6, V; VI, m. 49-50闂? 83.3, VII; and 2-methylfuran, b. 62-7闂? n²⁰_D 1.4362, 44.7, VIII. On the other hand, 1.5 g. dibenzoylmethane treated with 15 ml. XI, 6 ml. 50% XII, and 1.5 g. KOH by the modified method gave 1.3 g. 3,5-diphenylpyrazole, m. 199-200闂? while 0.5 g. BzCH₂CO₂H gave 0.22 g. 3-phenyl-5-pyrazolone (XIII), m. 234-5闂? while 1 g. 1,2-dibenzoylethane gave 0.8 g. 3,6-diphenylpyridazine (XIV), m. 221-2闂?(EtOH). Refluxing 5 g. PhCH:CHBz, 25 ml. XI, and 5 ml. 80% XII, and then treating with 3.2 g. KOH, diluting with H₂O, and extracting with ether gave 85.8% 1,2-diphenylcyclopropane, b₁₃ 171-5闂? n²⁰_D 1.5936. Similar treatment of methyl styryl ketone gave 68.1% 1-methyl-2-phenylcyclopropane (X), b. 187-9闂? n²⁰_D 1.5222. However, Me₂CH :CHAc gave 3,3,5-trimethylpyrazole (IX), b. 159-160闂? n²³_D 1.4542; HCl salt m. 173-4闂? It was postulated that the low b.p. of IX resulted in a low reflux temperature and prevented further decomposition into the cyclopropane derivative In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6COA of Formula: C9H5BrN2).

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. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. 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.Reference of 14204-27-4

The Mechanisms of Acid-Catalyzed Hydrolysis of N-(4-Substituted Arylthio)Phthalimides was written by Kutuk, Halil;Yakan, Hasan. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2011.Reference of 14204-27-4 This article mentions the following:

The acid-catalyzed hydrolysis of N-(4-substituted arylthio)phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acids at 40.0 闂?0.1 闂佺娅ｉ悡? Anal. of the data by the excess acidity method, activation parameters, and substituent effects indicates hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Reference of 14204-27-4).

Pan, Yixiao et al. published their research in Advanced Synthesis & Catalysis in 2022 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 5388-42-1

Cobalt-Catalyzed Selective Transformation of Levulinic Acid and Amines into Pyrrolidines and Pyrrolidinones using Hydrogen was written by Pan, Yixiao;Luo, Zhenli;Yang, Ji;Han, Jiahong;Yang, Jianbo;Yao, Zhen;Xu, Lijin;Wang, Peng;Shi, Qian. And the article was included in Advanced Synthesis & Catalysis in 2022.Reference of 5388-42-1 This article mentions the following:

Cobalt-catalyzed selective transformation of levulinic acid and primary amines into pyrrolidines and pyrrolidinones under H₂ was developed. The catalyst system consisting of Co(NTf₂)₂, 1,1,1-tris(di(4-methoxyphenyl)phosphinomethyl) ethane ((p-anisyl)triphos) and Me₃SiOTf works well for the synthesis of pyrrolidines via reductive amination/cyclization/deoxygenative reduction of amide, and using Co(NTf₂)₂/1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) as the catalyst under reduced hydrogen pressure results in exclusive formation of pyrrolidinones. Both aryl and alkyl primary amines are suitable substrates, and a variety of functional groups are tolerated. Meanwhile, 4-oxo-4-arylbutanoic acids, 5-oxohexanoic acid, 6-oxoheptanoic acid, 2-formylbenzoic acid, 2-acetylbenzoic acid and 2′-acetyl-[1,1′-biphenyl]-2-carboxylic acid are also applicable, allowing for convenient access to cyclic amines and lactams with different ring size. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Kumar, Vishal et al. published their research in Green Chemistry in 2012 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 5388-42-1

Synthesis of substituted amines and isoindolinones: catalytic reductive amination using abundantly available AlCl₃/PMHS was written by Kumar, Vishal;Sharma, Sushila;Sharma, Upendra;Singh, Bikram;Kumar, Neeraj. And the article was included in Green Chemistry in 2012.Recommanded Product: 5388-42-1 This article mentions the following:

AlCl₃ has been employed for highly chemoselective reductive amination of carbonyl compounds in ethanol using polymethylhydrosiloxane as an inexpensive, stable and safe reducing agent without an inert atm. A large range of functional groups such as nitro, carboxylic acid, acetyl, nitrile, halogen, methoxy, alkene and heterocycles were well tolerated. AlCl₃ also catalyzed tandem amination-amidation of 2-carboxybenzaldehyde with different amines to afford N-substituted isoindolinones, e.g., I (R = H, Me, MeO, Ac, I, NO₂). The catalyst can be recycled at least three times without any significant effect on activity and selectivity. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 5388-42-1).

Ditta, Jonathan L. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2013 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 5-Bromo-3-cyanoindole

Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors was written by Ditta, Jonathan L.;Denhart, Derek J.;Deskus, Jeffrey A.;Epperson, James R.;Meng, Zhaoxing;Gao, Qi;Mattson, Gail K.;LaPaglia, Mellissa A.;Taber, Matthew T.;Molski, Thaddeus F.;Lodge, Nicholas J.;Mattson, Ronald J.;Macor, John E.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Recommanded Product: 5-Bromo-3-cyanoindole This article mentions the following:

Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2-aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Recommanded Product: 5-Bromo-3-cyanoindole).

Shim, Sang Chul et al. published their research in Bulletin of the Korean Chemical Society in 1995 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. 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). Quality Control of 2-Phenylisoindolin-1-one

Synthesis of N-substituted isoindolin-1-ones via palladium-catalyzed carbonylative heterocyclization of o-bromobenzyl bromide with carbon monoxide and primary amines was written by Shim, Sang Chul;Jiang, Li Hong;Lee, Dong Yub;Cho, Chan Sik. And the article was included in Bulletin of the Korean Chemical Society in 1995.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

A convenient method for the synthesis of N-substituted isoindolin-1-ones is disclosed in palladium(0)-catalyzed heterocyclization of o-bromobenzyl bromide with carbon monoxide (CO) and primary amines in DMF at 100 闂佺娅ｉ悡? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).