10022-79-4

Basic information

• Product Name: 3H-Pyrido[3,4-b]indole, 4,9-dihydro-1-phenyl-
• Synonyms: 1-PHENYL-3,4-DIHYDROBETA-CARBOLINE;3H-Pyrido[3,4-b]indole,4,9-dihydro-1-phenyl;9H-1-phenyl-3,4-dihydropyrido<3,4-b>indole;1-phenyl-3,4-dihydro-1H-pyrido<3,4-b>indole
• CAS NO: 10022-79-4
• Molecular Formula: C17H14N2
• Molecular Weight: 246.312
• Mol File: 10022-79-4.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: 3H-Pyrido[3,4-b]indole, 4,9-dihydro-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Pyrido[3,4-b]indole, 4,9-dihydro-1-phenyl-(10022-79-4)
• EPA Substance Registry System: 3H-Pyrido[3,4-b]indole, 4,9-dihydro-1-phenyl-(10022-79-4)

Safety Data

• Hazardous Substances Data: 10022-79-4(Hazardous Substances Data)

Upstream product

• 126920-25-0 N-[2-(1-Benzyl-1H-indol-3-yl)-ethyl]-benzamide 
• 16979-93-4 (E)-N-(2-(1H-indol-3-yl)ethyl)-1-phenylmethanimine 
• 61-54-1 tryptamine 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 55-21-0 benzamide 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 4753-09-7 N-benzoyltryptamine 
• 17071-83-9 2,3,4,9-tetrahydro-1-phenyl-2-tosyl-1H-pyrido[3,4-b]indole 

Downstream Products

• 137689-13-5 2-Benzyl-1-methyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 137689-14-6 2-Benzyl-1,9-dimethyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 404926-00-7 1-methyl-1-phenyl-1,2,3,4-tetrahydro-β-carboline 
• 1240382-91-5 3-(4-fluorophenyl)-11b-phenyl-5,6,11,11b-tetrahydro[1,2,4]oxadiazolo[4',5':1,2]pyrido[3,4-b]indole 
• 1240382-96-0 (3-{2-[3,5-bis(4-fluorophenyl)-2-oxido-1H-1,2,4-triazol-1-yl]ethyl}-1H-indol-2-yl)(phenyl)methanone 
• 528602-90-6 C₃₄H₃₈N₂O₂ 
• 1198364-42-9 C₃₄H₃₈N₂O₂ 
• 114896-48-9 2-(4-methyl-1-piperazinyl)acetyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole 
• 114896-46-7 2-(chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole 
• 3574-01-4 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole hydrochloride 
• 142696-56-8 (S)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 148261-76-1 (R)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 16765-79-0 1-phenyl-9H-pyrido[3,4-b]indole 

Relevant articles and documents

Discovery of 3,3′-pyrrolidinyl-spirooxindoles as cardioprotectant prohibitin ligands

The scaffold proteins prohibitins-1 and 2 (PHB1/2) play many important roles in coordinating many cell signaling pathways and represent emerging targets in cardiology and oncology. We previously reported that a family of natural products derivatives, flavaglines, binds to PHB1/2 to exert cardioprotectant and anti-cancer effects. However, flavaglines also target the initiation factor of translation eIF4A, which doesn't contribute to cardioprotection and may even induce some adverse effects. Herein, we report the development of a convenient and robust synthesis of the new PHB2 ligand 2′-phenylpyrrolidinyl-spirooxindole, and its analogues. We discovered that these compounds displays cardioprotective effect against doxorubicin mediated cardiotoxicity and uncovered the structural requirement for this activity. We identified in particular some analogues that are more cardioprotectant than flavaglines. Pull-down experiments demonstrated that these compounds bind not only to PHB2 but also PHB1. These novel PHB ligands may provide the basis for the development of new drugs candidates to protect the heart against the adverse effects of anticancer treatments.

A simple method for the synthesis of 1-substituted β-carboline derivatives from tryptamine and carboxylic acids in polyphosphoric acid

A number of 1-substituted 3,4-dihydro-9H-β-carboline derivatives (4) with high purity and yields have been synthesized by treating of tryptamine (1) with carboxylic acids (2) in polyphosphoric acid. 3,4-Dihydro-9H-β-carbolines (4) were successfully transformed to 1,2,3,4-tetrahydro-9H-β-carbolines (5) and 9H-β-carbolines (6).{A figure is presented}.

Selectivity-tunable oxidation of tetrahydro-β-carboline over an OMS-2 composite catalyst: preparation and catalytic performance

Controlling the reaction selectivity of organic transformations without losing high conversion is always a challenge in catalytic processes. In this work, a H3PO4·12WO3/OMS-2 nanocomposite catalyst ([PW]-OMS-2) was prepared through the oxidation of a Mn(ii) salt with sodium phosphotungstate by KMnO4. Comprehensive characterization indicates that different Mn2+precursors significantly affected the crystalline phase and morphology of the as-synthesized catalysts and only MnSO4·H2O as the precursor could lead to a cryptomelane phase. Moreover, [PW]-OMS-2 demonstrated excellent catalytic activity toward aerobic oxidative dehydrogenation of tetrahydro-β-carbolines due to mixed crystalline phases, enhanced surface areas, rich surface oxygen vacancies and labile lattice oxygen species. In particular, β-carbolines and 3,4-dihydro-β-carbolines could be obtained from tetrahydro-β-carbolines with very high selectivity (up to 99%) over [PW]-OMS-2viatuning the reaction solvent and temperature. Under the present catalytic system, scalable synthesis of a β-carboline was achieved and the composite catalyst showed good stability and recyclability. This work not only clarified the structure-activity relationship of the catalyst, but also provided a practical pathway to achieve flexible, controllable synthesis of functional N-heterocycles.

The synthesis of 1,1-disubstituted tetrahydro-β-carbolines induced by iodine

A mild access to 1,1-disubstituted tetrahydro-β-carbolines is described. Tryptamine is subjected to Pictet-Spengler cyclization with various ketones using iodine.

A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple noyori-type catalysts in aqueous media

Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)-harmicine and (S)-crispine.

MnOx/catechol/H2O: A cooperative catalytic system for aerobic oxidative dehydrogenation of N-heterocycles at room temperature

Amorphous manganese oxide doped by Na+ ion (Na-AMO) was successfully prepared and found to be an efficient heterogeneous catalyst in aerobic oxidative dehydrogenation of N-heterocycles, cooperate with catechol. Na-AMO was fully characterized by XRD, XPS BET H2-TPR, CO2-TPD FT-IR, TEM, SEM and had rich amounts of surface absorbed active oxygen species which are responsible for superior catalytic performance. The synergistic interaction between Na-AMO and catechol makes catalytic system efficient and tolerant, which offers various N-heterocycles in good to excellent yields under mild conditions.

Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides

Ten types of Tf2O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf2O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill's modern version of the Bischler-Napieralski reaction. The value of the Tf2O/TTBP-based methodology was further demonstrated by the concise and high-yielding syntheses of several natural products.