52886-06-3

Usage

Uses

Used in Pharmaceutical Industry:
Hippadine is used as an antihistamine for treating allergic reactions, such as sneezing, itching, and runny nose, by blocking histamine's action.
Hippadine is also used as a cough suppressant to alleviate coughing caused by respiratory infections, providing relief by hindering the histamine-induced cough reflex.
Available in various forms like tablets, syrups, and injectable solutions, hippadine is typically administered orally. However, its use requires caution due to potential side effects like drowsiness, dizziness, and dry mouth, especially when combined with other sedating drugs.

InChI:InChI=1/C16H9NO3/c18-16-12-7-14-13(19-8-20-14)6-11(12)10-3-1-2-9-4-5-17(16)15(9)10/h1-7H,8H2

Upstream product

• 212-38-4 7H-1,3-Dioxolo-4,5-j-pyrrolo-3,2,1-de-phenanthridine 
• 476-28-8 2-epilycorine 
• 40360-71-2 anhydrolycorine-7-one 
• 116708-28-2 7H-[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-ol 
• 238750-23-7 7-oxo-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-5-carbaldehyde 
• 64-17-5 ethanol 
• 641-89-4 anhydrolycorine 
• 86449-39-0 6-bromo-benzo[1,3]dioxole-5-carboxylic acid ethyl ester 
• 548775-84-4 7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trimethylsilanyl-indole-1-carboxylic acid diethylamide 
• 665034-27-5 1-formyl-7-(3,4-methylenedioxyphenyl)indole 
• 180890-88-4 6,7-dihydro-9,10-methylenedioxypyrrolo[3,2,1-de]phenanthridine-4,5-dione 
• 51417-51-7 7-bromo-1H-indole 
• 61441-09-6 methyl 6-bromo-1,3-benzodioxole-5-carboxylate 
• 61599-80-2 methyl 6-iodo-2H-benzo1,3-dioxolene-5-carboxylate 

Downstream Products

• 88660-12-2 pratorimine 

Relevant academic research and scientific papers

Metal-free directed sp 2-C–H borylation

Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can

Synthesis of pyrrolophenanthridine alkaloids based on C(sp3)-H and C(sp2)-H functionalization reactions

Assoanine, pratosine, hippadine, and dehydroanhydrolycorine belong to the pyrrolophenanthridine family of alkaloids, which are isolated from plants of the Amaryllidaceae species. Structurally, these alkaloids are characterized by a tetracyclic skeleton that contains a biaryl moiety and an indole core, and compounds belonging to this class have received considerable interest from researchers in a number of fields because of their biological properties and the challenges associated with their synthesis. Herein, a strategy for the total synthesis of these alkaloids by using C-H activation chemistry is described. The tetracyclic skeleton was constructed in a stepwise manner by C(sp 3)-H functionalization followed by a Catellani reaction, including C(sp2)-H functionalization. A one-pot reaction involving both C(sp3)-H and C(sp2)-H functionalization was also attempted. This newly developed strategy is suitable for the facile preparation of various analogues because it uses simple starting materials and does not require protecting groups.

Electrochemical Total Synthesis of Pyrrolophenanthridone Alkaloids: Controlling the Anodically Initiated Electron Transfer Process

Electrochemical intramolecular C(sp2)-H cross-coupling and dehydrogenative indole synthesis were developed. Both reactions were initiated by anodic oxidation of the same electron-rich indoline moiety, but the product selectivity was controlled

Construction of pyrrolophenanthridinone scaffolds mediated by samarium(II) diiodide and access to natural product synthesis

Pyrrolophenanthridinone derivatives including the natural products were readily synthesized by samarium(II)-mediated reductive cyclization of aryl radical onto a benzene ring under mild reaction conditions. This methodology was applied to the concise synt

In search of a cytostatic agent derived from the alkaloid lycorine: Synthesis and growth inhibitory properties of lycorine derivatives

As a continuation of our studies aimed at the development of a new cytostatic agent derived from an Amaryllidaceae alkaloid lycorine, we synthesized 32 analogues of this natural product. This set of synthetic analogues included compounds incorporating sel

Simple synthesis of pratosine and hippadine by intramolecular palladium-catalyzed cyclization and decarboxylation

The palladium-catalyzed cyclization of dimethyl l-(2-bromo-4,5- dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenyl- phosphine)palladium(o) and potassium acetate in hot l,4-dioxane produced the 7H-pyrrolo[3,2,l-de]phenanthridine

Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles

Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright

Simple synthesis of amides and weinreb amides Using PPh3 or PolymerSupported PPh3 and Iodine

The combination of PPh3/I2 has been shown to be effective for the conversion of a range of carboxylic acids into secondary, tertiary, and Weinreb amides. Simplification of the procedure was possible with the use of polymer-supported PPh3/ I2. Weinreb amides produced with the use of polymer-supported PPh3 could be filtered through a short silica gel plug and used in further transformations. Thus, the use of polymer-supported PPh3 offers potential applicability to diversityoriented reactions. Formal total syntheses of apocynin and pratosine, as well as syntheses of anhydrolychorinone and hippadine, have been achieved through the use of this amide-forming method. An attempt has been made to gain insight into this reaction.

Comparative study of the Kumada, Negishi, Stille, and Suzuki - Miyaura reactions in the synthesis of the indole alkaloids hippadine and pratosine

The total synthesis of hippadine by a tandem metalation/cross-coupling/ lactamization strategy was investigated starting from either 7-bromoindole or a 6-halogenated methyl piperonate. The Kumada and Negishi cross-coupling reactions failed to provide any of the desired product. However, the Stille and Suzuki reactions furnished hippadine in low yields starting from the electron-deficient methyl 6-iodo- and 6-bromopiperonate, respectively. Starting from the metalated indole, only the Suzuki reaction occurred, affording hippadine in 67-74% and pratosine in 62% isolated yield.

A domino amidation route to indolines and indoles: Rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine

(Chemical Equation Presented) When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.