480-26-2

Usage

Uses

Used in Pharmaceutical Industry:
Cryptolepine is used as a therapeutic agent for its potential anti-cancer properties. It has been found to exhibit cytotoxic effects on various cancer cell lines, making it a promising candidate for the development of novel anti-cancer drugs.
Used in Chemical Research:
Cryptolepine serves as a valuable compound in chemical research, particularly in the study of alkaloids and their biological activities. Its unique structure allows scientists to explore its potential interactions with other molecules and its role in various biological processes.
Used in Drug Delivery Systems:
Similar to gallotannin, Cryptolepine can also be incorporated into drug delivery systems to improve its bioavailability and therapeutic outcomes. By using carriers such as organic and metallic nanoparticles, the limitations of Cryptolepine can be overcome, enhancing its delivery and efficacy against target cells or tissues.

InChI:InChI=1/C16H12N2/c1-18-15-9-5-2-6-11(15)10-14-16(18)12-7-3-4-8-13(12)17-14/h2-10H,1H3

Upstream product

• 243-58-3 quindoline 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 91-56-5 indole-2,3-dione 
• 109130-49-6 10H-indolo[3,2-d]quinoline-11-carboxylic acid 
• 120-72-9 indole 
• 5278-56-8 2-(o-nitrophenyl)quinoline 
• 577-59-3 2-acetylnitrobenzene 
• 874212-39-2 (Z)-3-Chloro-3-(2-nitro-phenyl)-propenal 
• 62-53-3 aniline 
• 5332-24-1 3-bromoquinoline 
• 108618-27-5 N-phenylquinolin-3-ylamine 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 

Relevant academic research and scientific papers

Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities

Using an ethnobotanical approach in combination with in vivo-guided fractionation as a means for lead discovery, cryptolepine was isolated as an antihyperglycemic component of Cryptolepis sanguinolenta. Two syntheses of cryptolepine, including an unambiguous synthesis, are reported. The hydroiodide, hydrochloride, and hydrotrifluoromethanesulfonate (hydrotriflate) salts of cryptolepine were synthesized, and a comparison of their spectral properties and their in vitro activities in a 3T3-L1 glucose transport assay is made. Cryptolepine and its salt forms lower blood glucose in rodent models of type II diabetes. While a number of bioactivities have been reported for cryptolepine, this is the first report that cryptolepine posesses antihyperglycemic properties.

Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi

Inspired by the widely antiphytopathogenic application of diversified derivatives from natural sources, cryptolepine and its derivatives were subsequently designed, synthesized, and evaluated for their antifungal activities against four agriculturally important fungi Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, and Sclerotinia sclerotiorum. The results obtained from in vitro assay indicated that compounds a1-a24 showed great fungicidal property against B. cinerea (EC50 4 μg/mL); especially, a3 presented significantly prominent inhibitory activity with an EC50 of 0.027 μg/mL. In the pursuit of further expanding the antifungal spectrum of cryptolepine, ring-opened compound f1 produced better activity with an EC50 of 3.632 μg/mL against R. solani and an EC50 of 5.599 μg/mL against F. graminearum. Furthermore, a3 was selected to be a candidate to investigate its preliminary antifungal mechanism to B. cinerea, revealing that not only spore germination was effectively inhibited and the normal physiological structure of mycelium was severely undermined but also detrimental reactive oxygen was obviously accumulated and the normal function of the nucleus was fairly disordered. Besides, in vivo curative experiment against B. cinerea found that the therapeutic action of a3 was comparable to that of the positive control azoxystrobin. These results suggested that compound a3 could be regarded as a novel and promising agent against B. cinerea for its valuable potency.

Application of A-ring modified cryptoxine derivative in prevention and treatment of agricultural plant diseases

The invention discloses application of any compound of A-ring modified cryptolepine derivatives L-1 to L-10 in prevention and treatment of agricultural plant diseases. Activity test results show thatthe compound has potential inhibitory activity on four p

2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles

A novel indole-2,3-epoxide equivalent, 2-hydroxyindoline-3-triethylammonium bromide, was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with various nucleophiles. By taking advantage of the nucleophilic character of the

Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed C H Bond Activation

N-tert-Butoxycarbonyl azide (BocN3) was shown to be an efficient and economic source for the directed introduction of N-Boc protected amino groups into the thiophene and benzene nucleus. Yields for the amination of 2-pyridin-2-ylthiophenes (10 examples) were 52–88%. For the amination of the respective benzenes (10 examples) yields between 54% and 99% were recorded with an improved reactivity observed for substrates that bear an electron-withdrawing group. The reaction was applied to short total syntheses of the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp3) H bond amination and to the amination of 2-phenyloxazoline. For the amination of 2-pyridin-2-ylbenzene a kinetic deuterium isotope effect of 2.0 was determined. (Figure presented.) .

NMR determination of pKa values of indoloquinoline alkaloids

Malaria is one of the most serious global health problems. Isolating new therapeutic agents with potential antimalarial activity from natural sources or preparing such agents either semisynthetically or synthetically is one strategy for solving the proble

A concise synthesis of the DNA-intercalating and antimalarial alkaloid cryptolepine and its fluorescence behaviour in solvents of different polarities

A microwave-induced rapid and facile synthesis of the DNA-intercalating and antimalarial drug cryptolepine is described. The key step in this synthesis involves the aqueous-phase base-catalyzed condensation of isatin and 1-acetyl-1H-indol-3-yl acetate which has been simplified and expedited by dielectric heating, employing an ordinary domestic microwave oven. The method transforms the synthesis of an important drug molecule from a prohibitively lengthy process to a matter of a few minutes with a much improved yield. Dual absorption and fluorescence is observed from the molecular system in solvents of different polarity thus providing valuable insight into its binding modes toward protein or DNA.

Thermal cyclization of 3-arylamino-3-(2-nitrophenyl)-propenal Schiff base hydrochlorides followed by triethyl phosphite mediated deoxygenation: A facile synthesis of quindolines

A simple and useful method for the synthesis of various 2-substituted quindolines starting from 2-nitroacetophenone is described.

Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives

A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents.

New synthesis of benzo-δ-carbolines, cryptolepines, and their salts: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-carbolines, benzo-δ-carbolines, and cryptolepines

The paper describes, in its first part, a new synthesis of benzo-δ-carbolines, cryptolepines, and their salts. The strategy is based on the association between halogen-dance and hetero-ring cross-coupling. It is fully convergent and regioselective with in