20/10/2022 - Page 4 of 8 - Indole Building Blocks

Shi, Jingxin’s team published research in Bioresource Technology in 2019 | 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.Reference of 1H-Indole

Reference of 1H-IndoleIn 2019 ,《Enhanced biodegradation of coal gasification wastewater with anaerobic biofilm on polyurethane (PU), powdered activated carbon (PAC), and biochar》 appeared in Bioresource Technology. The author of the article were Shi, Jingxin; Han, Yuxing; Xu, Chunyan; Han, Hongjun. The article conveys some information:

The primary objective was to explore the feasibility of anaerobic biofilm on polyurethane (PU), powd. activated carbon (PAC), and biochar in strengthening anaerobic degradation of phenolic compounds and selected nitrogen heterocyclic compounds (NHCs) in coal gasification wastewater (CGW). When total phenols (TPh) was less than 300 mg/L, PAC-based biofilm was more efficient. Whereas, when the TPh concentration was more than 450 mg/L, PU-based biofilm performed the optimal degradation efficiency. Furthermore, microbial community structure anal. showed that PAC and biochar had little effect on the microbial community structure after 120 days of operation, while the addition of PU could lead to the enrichment of Giesbergeria, Caldisericum, Thauera, Methanolinea, and Methanoregula. The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Reference of 1H-Indole)

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

Dan, Akihito’s team published research in Carbohydrate Letters in 1996 | 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.

Dan, Akihito; Ito, Yukishige; Ogawa, Tomoya published their research in Carbohydrate Letters on February 29 ,1996. The article was titled 《An efficient synthetic route to bisecting N-acetylglucosamine containing asparagine-linked glycan》.Related Products of 99409-32-2 The article contains the following contents:

A fully stereocontrolled and concise synthetic route to bisecting GlcNAc-containing oligosaccharide is described. The pentasaccharide, which was synthesized previously, by p-methoxybenzyl-assisted β-mannosidation as the key transformation, was reacted with N-phthaloyl-protected glucosamine donor. The desired product obtained was further deprotected into oligosaccharide I, which corresponds to the hexasaccharide region of bisecting GlcNAc-containing Asn-linked glycans. In the experimental materials used by the author, we found Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Related Products of 99409-32-2)

Knepper, Kerstin’s team published research in Organic Letters in 2003 | CAS: 588688-45-3

7-Chloro-1H-indole-4-carboxylic acid(cas: 588688-45-3) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Synthetic Route of C9H6ClNO2

Knepper, Kerstin; Brase, Stefan published their research in Organic Letters on August 7 ,2003. The article was titled 《Bartoli Indole Synthesis on Solid Supports》.Synthetic Route of C9H6ClNO2 The article contains the following contents:

Bartoli indole synthesis was performed on solid supports. Starting from Merrifield resin, immobilization of five nitrobenzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted Me indolecarboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester moieties, and tolerance of o,o’-unsubstituted nitro resins. Heck and Sonogashira reactions are also possible with immobilized indoles. In the part of experimental materials, we found many familiar compounds, such as 7-Chloro-1H-indole-4-carboxylic acid(cas: 588688-45-3Synthetic Route of C9H6ClNO2)

Vaidya, Gargi Nikhil’s team published research in Green Chemistry 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.SDS of cas: 399-52-0

In 2019,Green Chemistry included an article by Vaidya, Gargi Nikhil; Fiske, Sneha; Verma, Hansa; Lokhande, Shyam Kumar; Kumar, Dinesh. SDS of cas: 399-52-0. The article was titled 《A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water》. The information in the text is summarized as follows:

A modular and selective C-H arylation of indoles I (R = 5-CN, 5-OCH3, 6-Cl, etc.; R1 = H, Me) following the micellar catalysis approach using the third generation “”designer”” surfactant SPGS-550-M in the presence of 1 mol of [(cinnamyl)PdCl]2 under mild conditions has been described. Thus, access to high value C-3-arylated indoles II [R2 = H, F, MeO, CF3, C(O)Me] and C-2-arylated indoles III (Ar = Ph, 4-fluorophenyl, 2H-1,3-benzodioxol-5-yl) was achieved by fulfilling the “”triple bottom line philosophy”” of green chem. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, resp. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields. The results came from multiple reactions, including the reaction of 5-Fluoro-1H-indole(cas: 399-52-0SDS of cas: 399-52-0)

Zhou, Su’s team published research in Organic Chemistry Frontiers in 2021 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).SDS of cas: 399-52-0

Zhou, Su; Liu, Qianqian; Bao, Ming; Huang, Jie; Wang, Junjian; Hu, Wenhao; Xu, Xinfang published an article in 2021. The article was titled 《Gold(I)-catalyzed redox transformation of o-nitroalkynes with indoles for the synthesis of 2,3′-biindole derivatives》, and you may find the article in Organic Chemistry Frontiers.SDS of cas: 399-52-0 The information in the text is summarized as follows:

An efficient and practical methods for the syntheses of 2-indolyl indolone N-oxides I [R = H, Me, CH2CH=CH2; R1 = 4-F, 5-Cl, 6-Me, etc.; R2 = H, 6-Me, 7-F, etc.; R3 = H, Me] and 1’H,3H-[2,3′-biindol]-3-ones II [R4 = H, Ph, Bn, 4-ClPhCH2; R5 = H, 6-Me, 5-F, 7-F ] via gold(I)-catalyzed cascade reaction of o-nitroalkynes with indoles were reported. The generated product could be readily converted into the 2-indolylbenzoxazinone, which emitted strong blue fluorescence. Also some of the compounds I and II evaluated for antitumor activity for small cell lung cancer and the results showed that compounds I [R = H; R1 = 6-Me; R2 = H; R3 = H] and II [R4 = H; R5 = 6-Me] exhibited high anticancer potency against SCLC cells. In addition to this study using 5-Fluoro-1H-indole, there are many other studies that have used 5-Fluoro-1H-indole(cas: 399-52-0SDS of cas: 399-52-0) was used in this study.

Mullins, Terry’s team published research in Nature Communications in 2022 | CAS: 120-72-9

In 2022,Mullins, Terry; Karamatskos, Evangelos T.; Wiese, Joss; Onvlee, Jolijn; Rouzee, Arnaud; Yachmenev, Andrey; Trippel, Sebastian; Kuepper, Jochen published an article in Nature Communications. The title of the article was 《Picosecond pulse-shaping for strong three-dimensional field-free alignment of generic asymmetric-top molecules》.Formula: C8H7N The author mentioned the following in the article:

Fixing mols. in space is a crucial step for the imaging of mol. structure and dynamics. Here, we demonstrate three-dimensional (3D) field-free alignment of the prototypical asym. top mol. indole using elliptically polarized, shaped, off-resonant laser pulses. A truncated laser pulse is produced using a combination of extreme linear chirping and controlled phase and amplitude shaping using a spatial-light-modulator (SLM) based pulse shaper of a broadband laser pulse. The angular confinement is detected through velocity-map imaging of H+ and C2+ fragments resulting from strong-field ionization and Coulomb explosion of the aligned mols. by intense femtosecond laser pulses. The achieved three-dimensional alignment is characterized by comparing the result of ion-velocity-map measurements for different alignment directions and for different times during and after the alignment laser pulse to accurate computational results. The achieved strong three-dimensional field-free alignment of cos2δ = 0.89 demonstrates the feasibility of both, strong three-dimensional alignment of generic complex mols. and its quant. characterization.1H-Indole(cas: 120-72-9Formula: C8H7N) was used in this study.

Kumari, Archana’s team published research in Bioorganic Chemistry in 2019 | CAS: 120-72-9

Name: 1H-IndoleIn 2019 ,《Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives》 appeared in Bioorganic Chemistry. The author of the article were Kumari, Archana; Singh, Rajesh K.. The article conveys some information:

A review. Indole is a versatile pharmacophore, a privileged scaffold and an outstanding heterocyclic compound with wide ranges of pharmacol. activities due to different mechanisms of action. It is an superlative moiety in drug discovery with the sole property of resembling different structures of the protein. Plenty of research has been taking place in recent years to synthesize and explore the various therapeutic prospectives of this moiety. This review summarizes some of the recent effective chem. synthesis (2014-2018) for indole ring. This review also emphasized on the structure-activity relationship (SAR) to reveal the active pharmacophores of various indole analogs accountable for anticancer, anticonvulsant, antimicrobial, antitubercular, antimalarial, antiviral, antidiabetic and other miscellaneous activities which have been investigated in the last five years. The precise features with motives and framework of each research topic is introduced for helping the medicinal chemists to understand the perspective of the context in a better way. This review will definitely offer the platform for researchers to strategically design diverse novel indole derivatives having different promising pharmacol. activities with reduced toxicity and side effects. In the experimental materials used by the author, we found 1H-Indole(cas: 120-72-9Name: 1H-Indole)

Grugel, Christian P.’s team published research in Organic Letters in 2019 | CAS: 399-52-0

《Rhodium-Catalyzed Diastereo- and Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines》 was written by Grugel, Christian P.; Breit, Bernhard. HPLC of Formula: 399-52-0This research focused onvinylic spiroindoline preparation enantioselective diastereoselective rhodium catalyst; allenylindole spirocyclization reduction. The article conveys some information:

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction’s synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0HPLC of Formula: 399-52-0)

Takeuchi, Kazuya’s team published research in Chemistry Letters in 2000 | 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.HPLC of Formula: 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.

HPLC of Formula: 99409-32-2On June 5, 2000, Takeuchi, Kazuya; Tamura, Takayuki; Jona, Hideki; Mukaiyama, Teruaki published an article in Chemistry Letters. The article was 《A novel activating agents of “”disarmed”” thioglycosides, combination of trityl tetrakis(pentafluorophenyl)borate, iodine and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)》. The article mentions the following:

A combined use of trityl tetrakis(pentafluorophenyl) borate [TrB(C6F5)4], iodine (I2) and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) effectively activates “”disarmed”” thioglycosides to afford the corresponding disaccharides in high yields on treatment with several glycosyl acceptors. The results came from multiple reactions, including the reaction of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2HPLC of Formula: 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.HPLC of Formula: 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.

Chu, N. T.’s team published research in Journal of Food Science in 1976 | CAS: 59132-30-8

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8) 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.Computed Properties of C13H12N2O4They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

In 1976,Journal of Food Science included an article by Chu, N. T.; Clydesdale, F. M.. Computed Properties of C13H12N2O4. The article was titled 《Reactions between amino acids and organic acids: reaction of tryptophan and pyruvic acid》. The information in the text is summarized as follows:

Pyruvic acid reacted with tryptophan, to give yellow products. Four compounds were isolated: 3 were identified as 1,2,3,4-tetrahydroharman-1,3-dicarboxylic acid, an isomer of 1,2,3,4-tetrahydroharman-1,3-dicarboxylic acid and harman. The compound not fully identified, was a yellow polymer. The ratio of pyruvic acid to tryptophan used in this reaction was approx. 1.6:1. The reaction proceeded via a 1:1 mol. reaction between tryptophan and pyruvic acid to form 1,2,3,4-tetrahydroharman-1,3-dicarboxylic acid and its yellow isomer followed by the formation of a yellow polymer produced by the interaction of the yellow isomer of 1,2,3,4-tetrahydroharman-1,3-dicarboxylic acid and pyruvic acid. In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8Computed Properties of C13H12N2O4)