October 2022 - Page 18 of 72 - Indole Building Blocks

Minuth, Tobias’s team published research in Synlett in 2008 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Related Products of 99409-32-2They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Related Products of 99409-32-2On June 13, 2008, Minuth, Tobias; Boysen, Mike M. K. published an article in Synlett. The article was 《A general and efficient route to 3-O-modified carbohydrate bis(oxazoline) ligands》. The article mentions the following:

An efficient route to derivatives of carbohydrate-based bis(oxazoline) ligands with 3-O substituents of varying steric demand is described. The synthesis of the new ligands proceeds via a thioglucoside key intermediate. The double cyclization to the desired bis(oxazolines) is initiated with N-iodosuccinimide under mild conditions. Employing this strategy, four new 3-O-modified bis(oxazoline) ligands were obtained in good yields. In addition to this study using Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside, there are many other studies that have used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Related Products of 99409-32-2) was used in this study.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Tang, Zhi’s team published research in Organic Letters in 2019 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Product Details of 399-52-0

In 2019,Organic Letters included an article by Tang, Zhi; Liu, Zhili; Tong, Zhou; Xu, Zhihui; Au, Chak-Tong; Qiu, Renhua; Kambe, Nobuaki. Product Details of 399-52-0. The article was titled 《Cu-Catalyzed Cross-Dehydrogenative Coupling of Heteroaryl C(sp2)-H and Tertiary C(sp3)-H Bonds for the Construction of All-Carbon Triaryl Quaternary Centers》. The information in the text is summarized as follows:

A Cu-catalyzed protocol for cross-dehydrogenative coupling of benzofuranones with quinolines, indoles, carbazoles, and thiophene, which furnishes highly functionalized 3,3-diaryl benzofuranones bearing a three aryl quaternary carbon center at the C3 position in good yields, has been developed. A radical mechanism is proposed. In the part of experimental materials, we found many familiar compounds, such as 5-Fluoro-1H-indole(cas: 399-52-0Product Details of 399-52-0)

Mohr, Yorck’s team published research in ACS Catalysis in 2020 | CAS: 399-52-0

《Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group》 was written by Mohr, Yorck; Renom-Carrasco, Marc; Demarcy, Clement; Quadrelli, Elsje Alessandra; Camp, Clement; Wisser, Florian M.; Clot, Eric; Thieuleux, Chloe; Canivet, Jerome. COA of Formula: C8H6FN And the article was included in ACS Catalysis in 2020. The article conveys some information:

A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position was reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 arylation of indoles with high turnover numbers This catalytic system was successfully applied to a wide range of substrates including various functional aryl halides and indolic cores. The unique role of LiHMDS as both a base and unexpected transient directing group was revealed exptl. and elucidated computationally, in line with a Heck-type insertion-elimination mechanism. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0COA of Formula: C8H6FN)

Dhuguru, Jyothi’s team published research in Molecules in 2020 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. 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.Application of 120-72-9

Application of 120-72-9In 2020 ,《Role of indole scaffolds as pharmacophores in the development of anti-lung cancer agents》 appeared in Molecules. The author of the article were Dhuguru, Jyothi; Skouta, Rachid. The article conveys some information:

A review. Lung cancer is the leading cause of death in men and women worldwide, affecting millions of people. Between the two types of lung cancers, non-small cell lung cancer (NSCLC) is more common than small cell lung cancer (SCLC). Besides surgery and radiotherapy, chemotherapy is the most important method of treatment for lung cancer. Indole scaffold is considered one of the most privileged scaffolds in heterocyclic chem. Indole may serve as an effective probe for the development of new drug candidates against challenging diseases, including lung cancer. In this review, we will focus on discussing the existing indole based pharmacophores in the clin. and pre-clin. stages of development against lung cancer, along with the synthesis of some of the selected anti-lung cancer drugs. Moreover, the basic mechanism of action underlying indole based anti-lung cancer treatment, such as protein kinase inhibition, histone deacetylase inhibition, DNA topoisomerase inhibition, and tubulin inhibition will also be discussed. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Application of 120-72-9)

Zhao, Peizheng’s team published research in ChemCatChem in 2020 | CAS: 399-52-0

《Copper-Catalyzed Aerobic Oxidative Amination of Indole Derivatives via Single-Electron Transfer》 was written by Zhao, Peizheng; Wang, Ke; Yue, Yuanyuan; Chao, Junli; Ye, Yaqing; Tang, Qinghu; Liu, Jianming. Related Products of 399-52-0 And the article was included in ChemCatChem in 2020. The article conveys some information:

An efficient and clean approach for the oxidative amination of indole derivatives with phenothiazines is developed under copper-catalyzed aerobic conditions. The reaction is carried out via the cross-coupling of indole radical cation and phenothiazine radical in air. This approach offers a new perspective in the application of phenothiazine as a nitrogen group source for C-N bond formation reactions. The experimental process involved the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Related Products of 399-52-0)

Shaikh, Iqbal N.’s team published research in Molecules in 2021 | CAS: 399-52-0

Shaikh, Iqbal N.; Rahim, Abdul; Faazil, Shaikh; Adil, Syed Farooq; Assal, Mohamed E.; Hatshan, Mohammad Rafe published an article in 2021. The article was titled 《BF3-OEt2 catalyzed C3-alkylation of indole: synthesis of indolylsuccinimides and their cytotoxicity studies》, and you may find the article in Molecules.Recommanded Product: 5-Fluoro-1H-indole The information in the text is summarized as follows:

A simple and efficient BF3-OEt2 promoted C3-alkylation of indole has been developed to obtain 3-indolylsuccinimides I (R1 = H, OMe, F, Br, CN, NO2; R2 = H, Me, Bn; R3 = Me, Ph, Bn) from com. available indoles II and maleimides III, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, I (R1 = H, R2 = R3 = Me), having N,N-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC50 value 0.02μM and 0.8μM against HT-29 and Hepg2 cell lines, resp., and compound I (R1 = R2 = H, R3 = Bn) was most active amongst the series with IC50 value 1.5μM against A549 cells. Mol. docking study and mechanism of reaction have briefly been discussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 5-Fluoro-1H-indole)

Chen, Shuyou’s team published research in ACS Catalysis in 2019 | CAS: 120-72-9

Reference of 1H-IndoleIn 2019 ,《C2/C4 Regioselective Heteroarylation of Indoles by Tuning C-H Metalation Modes》 appeared in ACS Catalysis. The author of the article were Chen, Shuyou; Zhang, Min; Su, Rongchuan; Chen, Xingyu; Feng, Boya; Yang, Yudong; You, Jingsong. The article conveys some information:

The development of a rational strategy to achieve the complete regioselectivity and the capability to switch regioselectivity is an appealing, yet challenging, puzzle in transition-metal-catalyzed oxidative Ar-H/Ar-H cross-coupling. Disclosed herein is an iridium-catalyzed C2/C4 regioselective C-H heteroarylation of indoles with the help of a pivaloyl group at the C3 position. The judicious choice of the catalytic systems allows the C2-heteroarylation of indole via a concerted metalation-deprotonation (CMD) process and the C4-heteroarylation via a trimol. electrophilic substitution (SE3) pathway. The oxidants Cu(OAc)2·H2O and Ag2O are demonstrated to play a vital role in the C2/C4 regioselectivity. In this Article, a heteroaryl-Ir(III)-heteroaryl complex prior to reductive elimination is successfully isolated and characterized, which represents the first example of capturing the bis(hetero)aryl metallic intermediate in oxidative Ar-H/Ar-H cross-coupling. The regiodivergent heteroarylation of indoles developed herein provides an opportunity to rapidly assemble diverse C4- and C2-heteroarylated indoles. The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Reference of 1H-Indole)

Kelly, R. J.’s team published research in HortScience in 1983 | CAS: 60096-23-3

Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3) is auxin-family plant hormone, and is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.Name: Potassium 4-(1H-indol-3-yl)butanoate

Kelly, R. J.; Moser, B. C. published their research in HortScience on December 31 ,1983. The article was titled 《Influence of temperature and auxin on root regeneration by seedlings of Liriodendron tulipifera L》.Name: Potassium 4-(1H-indol-3-yl)butanoate The article contains the following contents:

Root regeneration and shoot growth of seedlings of L. tulipifera (tulip tree) increased as temperature of either the soil or aerial growing environment increased from 10° to 21°. IBA K salt [60096-23-3] applied to the tap roots at 1000 mg/L, increased root regeneration and shoot growth when both air and soil temperatures were at 15.5° or 21°. When air temperature was maintained at 21° and soil temperature was varied from 10° to 21°, root regeneration and shoot growth increased as soil temperature increased. IBA increased root regeneration only when soil temperature was 21°. In the experiment, the researchers used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Name: Potassium 4-(1H-indol-3-yl)butanoate)

Li, Guofeng’s team published research in Organic Letters in 2019 | CAS: 399-52-0

The author of 《Switchable Skeletal Rearrangement of Dihydroisobenzofuran Acetals with Indoles》 were Li, Guofeng; Yao, Ying; Wang, Zheng; Zhao, Man; Xu, Jiecheng; Huang, Liwu; Zhu, Gongming; Bao, Guangjun; Sun, Wangsheng; Hong, Liang; Wang, Rui. And the article was published in Organic Letters in 2019. Computed Properties of C8H6FN The author mentioned the following in the article:

The switchable skeletal rearrangement for the construction of amino indanones and tetrahydroisoquinolones frameworks had been developed. In the presence of a chiral phosphoric acid catalyst, the reaction gave the amino indanones in high yields and good to excellent ee (85-98%), while the methoxyl substituent at the 5-position of dihydroisobenzofuran acetal selectively gave isoquinolinones products in good to excellent ee (46-98%). Furthermore, DFT calculations were performed to explain the regioselectivity of the switchable transformation pathways. The experimental process involved the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN)

Liu, Xuelei’s team published research in Organic Letters in 2019 | CAS: 120-72-9

The author of 《Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes》 were Liu, Xuelei; Ma, Shuang; Toy, Patrick H.. And the article was published in Organic Letters in 2019. SDS of cas: 120-72-9 The author mentioned the following in the article:

The use of a halogen bond donor to catalyze Friedel-Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analog, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.1H-Indole(cas: 120-72-9SDS of cas: 120-72-9) was used in this study.