20/02/2023 - Page 11 of 14 - Indole Building Blocks

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).

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

Lesniewski, Joseph M. et al. published their research in Proceedings of International Wire and Cable Symposium in 1980 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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.Category: indole-building-block

Comparison of the relative cost effectiveness of brominated and chlorinated flame retardants in EPDM was written by Lesniewski, Joseph M.. And the article was included in Proceedings of International Wire and Cable Symposium in 1980.Category: indole-building-block This article mentions the following:

The relative effectiveness of cyclooctadiene-hexachlorocyclopentadiene Diels-Alder diadduct (I) [13560-89-9] and tetrabromophthalimide (II) [24407-32-7] as flame retardants was studied in calcined clay-filled 80:20 (weight) EPDM rubber-polyethylene [9002-88-4] standard formulations (revised NDX 5117) for wire and cable applications. The flame retardant component was removed from the standard formulation (containing 30 parts flame retardant) until 0, 10, 15, 20, or 30% removal of fire retardant was obtained. The 200% modulus was higher and % elongation was slightly lower for formulations containing II. Ratings from the O index test indicated a better response from II than from I in all formulations. The UL-94 flame test indicated that only the standard formula and the formula with 10% removal of II gave a 94-VO rating; the formula containing I burned under UL-94 testing. The VW-1 flame test indicated that the standard loading for I was at its optimum for the system and that further lowering resulted in failure; the amount of II was lowered by 闂?0% before failing the VW-1 test. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Category: indole-building-block).

Semenya, Dorothy et al. published their research in ACS Medicinal Chemistry Letters in 2022 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C9H6ClNO

Structural Rigidification of N-Aryl-pyrroles into Indoles Active against Intracellular and Drug-Resistant Mycobacteria was written by Semenya, Dorothy;Touitou, Meir;Ribeiro, Camila Maringolo;Pavan, Fernando Rogerio;Pisano, Luca;Singh, Vinayak;Chibale, Kelly;Bano, Georg;Toscani, Anita;Manetti, Fabrizio;Gianibbi, Beatrice;Castagnolo, Daniele. And the article was included in ACS Medicinal Chemistry Letters in 2022.Computed Properties of C9H6ClNO This article mentions the following:

A series of indolyl-3-methyleneamines incorporating lipophilic side chains were designed through a structural rigidification approach and synthesized for investigation as new chem. entities against Mycobacterium tuberculosis (Mtb). The screening led to the identification of a 6-chloroindole analog 7j (I) bearing an N-octyl chain and a cycloheptyl moiety, which displayed potent in vitro activity against laboratory and clin. Mtb strains, including a pre-extensively drug-resistant (pre-XDR) isolate. 7j also demonstrated a marked ability to restrict the intracellular growth of Mtb in murine macrophages. Further assays geared toward mechanism of action elucidation have thus far ruled out the involvement of various known promiscuous targets, thereby suggesting that the new indole 7j may inhibit Mtb via a unique mechanism. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

Song, Zhuang et al. published their research in European Journal of Medicinal Chemistry in 2016 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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 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). Recommanded Product: 5-Isopropylindoline-2,3-dione

Design, synthesis, and biological evaluation of (2E)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate derivatives as anti-proliferative agents through ROS-induced cell apoptosis was written by Song, Zhuang;Chen, Cai-Ping;Liu, Jun;Wen, Xiaoan;Sun, Hongbin;Yuan, Haoliang. And the article was included in European Journal of Medicinal Chemistry in 2016.Recommanded Product: 5-Isopropylindoline-2,3-dione This article mentions the following:

A novel class of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetate derivatives I [R = H, Me, Bn; R¹ = OMe, NMe, OC₆H₅, etc.; R² = H, 5-Me, 5-Cl, etc.] and (2-oxo-1,2-dihydro-3H-indol-3-yl)acetate derivatives II [R = H, Me; R¹ = Me, t-Bu] were designed and synthesized. Their in vitro anti-proliferative activity was evaluated against different cancer cell lines, including SK-BR-3, MDA-MB-231, HCT-116, SW480, Ovcar-3, HL-60, Saos-2 and HepG2. The results showed that, compound I [R = H; R¹ = Ot-Bu; R² = H] (IC₅₀ = 2.45 濠电偞鎸鹃幏?, I [R = Me; R¹ = Ot-Bu; R² = H] (IC₅₀ = 2.76 濠电偞鎸鹃幏? and I [R = H; R¹ = Ot-Bu; R² = 5-Cl] (IC₅₀ = 3.16 濠电偞鎸鹃幏? were the most potent ones against HL-60. Further biol. assays showed that HL-60, HCT116 and MDA-MB-231 were the most sensitive cell lines for compound I [R = H; R¹ = Ot-Bu; R² = H] and I [R = H; R¹ = Ot-Bu; R² = 5-Cl]. Mechanistic study revealed that compound I [R = H; R¹ = Ot-Bu; R² = H] enhanced reactive oxygen species level by inhibiting TrxR and then induced apoptosis by activating apoptosis proteins, bax and cleaved-caspase-3 in HCT116 cells. SAR anal. showed that the double bond in this series of compounds was very important for their cytostatic activity, indicating that the Michael-acceptor structure might contribute greatly to the anti-proliferative activity. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 5-Isopropylindoline-2,3-dione).

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).

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).

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).

Heda, L. C. et al. published their research in E-Journal of Chemistry in 2009 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Category: indole-building-block

Synthesis and antimicrobial activity of some derivatives of 5-substituted indole dihydropyrimidines was written by Heda, L. C.;Sharma, Rashmi;Pareek, C.;Chaudhari, P. B.. And the article was included in E-Journal of Chemistry in 2009.Category: indole-building-block This article mentions the following:

Haloindole substituted dihydropyrimidines I (R = H, Br, Cl, I; X = O or S) have been prepared via Bignelli reaction of haloformylindoles with urea (or thiourea) and ethylacetoacetate. I were evaluated for their antibacterial and antifungal activity with the min. inhibitory concentration (MIC) determined by micro dilution technique in Mueller-Hinton broth. The MICs were recorded after 24 h of incubation at 37闂? These results are promising, showing these compounds are biol. active. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

Tan, Wei et al. published their research in RSC Advances in 2013 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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 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). Application of 774-47-0

Diversity-oriented synthesis of spiro-oxindole-based 2,5-dihydropyrroles via three-component cycloadditions and evaluation on their cytotoxicity was written by Tan, Wei;Zhu, Xiao-Tong;Zhang, Shu;Xing, Gui-Juan;Zhu, Ren-Yi;Shi, Feng. And the article was included in RSC Advances in 2013.Application of 774-47-0 This article mentions the following:

The construction of a spiro-oxindole-based 2,5-dihydropyrrole scaffold I (R = H, Me, Ph, etc.; R¹ = H, 4-Cl, 5-OMe, etc.; R² = Me, Et) with potential bioactivity has been established via an efficient three-component reaction of isatin, amino-ester and alkyne. This protocol represents the first 1,3-dipolar cycloaddition of electron-deficient alkynes with isatin-derived azomethine ylides, providing an easy access to spiro-oxindole-based 2,5-dihydropyrroles with structural diversity in high yields (up to 99%). In addition, the bioscreen of these new spiro-dihydropyrroles has led to the finding of sixteen compounds with promising cytotoxicity to MCF-7 cells. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Application of 774-47-0).

Jayaraman, Arumugam et al. published their research in Tetrahedron 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 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). Synthetic Route of C8H6N2O2

Revisiting the reduction of indoles by hydroboranes: A combined experimental and computational study was written by Jayaraman, Arumugam;Powell-Davies, Henry;Fontaine, Frederic-Georges. And the article was included in Tetrahedron in 2019.Synthetic Route of C8H6N2O2 This article mentions the following:

A combined exptl. and d. functional computational study was used to probe the mechanism for the reduction of indoles using simple borane BH₃闁荤姾娅ｉ弸宄係 (DMS = di-Me sulfide). Exptl. and computational studies all steer to the formation of the reduced species 1-BH₂-indolines as the resting state for this reaction, as opposed to the historically presumed formation of the unreduced 1-BH₂-indoles, before the addition of a proton source to form the final product indolines. Furthermore, it was observed that mol. H₂ was generated and consumed in the reaction. Computations put forward hydroboration followed by protodeborylation as the very reasonable mechanistic route for the formation of exptl. observed major intermediate 1-BH₂ indolines. For the H₂ consumption in the reaction, computations suggest the frustrated Lewis pair-type heterolytic splitting of H₂ by a bis(3-indolinyl)borane intermediate. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).