isocryptolepine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

isocryptolepine: synthetic antimalarial alkaloid; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	380925
CHEMBL ID	596333
CHEMBL ID	502768
SCHEMBL ID	9390637
MeSH ID	M0580893

Synonyms (15)

Synonym
NCI60_023278
crytosanguinolentine
nsc666709
nsc-666709
inchi=1/c16h12n2/c1-18-10-13-11-6-2-4-8-14(11)17-16(13)12-7-3-5-9-15(12)18/h2-10h,1h
5h-indolo[3,2-c]quinoline, 5-methyl-
5-methyl-5h-indolo[3,2-c]quinoline
5-methylindolo[3,2-c]quinoline
isocryptolepine
CHEMBL596333
CHEMBL502768 ,
bdbm50412203
SCHEMBL9390637
165467-65-2
DTXSID601296862

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay ID	Title	Year	Journal	Article
AID1140207	Selectivity index, ratio of IC50 for rat L6 cells to IC50 for chloroquine/pyrimethamine-resistant Plasmodium falciparum K1	2014	Bioorganic & medicinal chemistry, May-01, Volume: 22, Issue:9	Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11.
AID1858965	Antiproliferative activity against human HuCC-A1 cells assessed as cell growth inhibition	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1201072	Cytotoxicity against human HuCCa1 cells by MTT assay	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID453261	Displacement of methyl green dye from DNA	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID1201071	Cytotoxicity against human HepG2 cells by MTT assay	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201062	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for chloroquine-resistant Plasmodium falciparum 3D7	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201064	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for chloroquine/mefloquine-resistant Plasmodium falciparum SKF58	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1858961	Selectivity index, ratio of CC50 for rat L6 cells to IC50 for Plasmodium falciparum K1 infected in rat L6 cells	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1201065	Antiplasmodial activity against chloroquine/mefloquine-resistant Plasmodium falciparum SRIV35	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201058	Cytotoxicity against human MRC5 cells by MTT assay	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1858967	Antiproliferative activity against human MOLT-3 cells assessed as cell growth inhibition	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1201061	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID453260	Inhibition of beta-hematin formation by BHIA assay	2009	Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20	Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID1201077	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for human MOLT3 cells	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1140206	Antimalarial activity against erythrocytic stage of chloroquine/pyrimethamine-resistant Plasmodium falciparum K1 after 48 hrs by [3H]-hypoxanthine incorporation assay	2014	Bioorganic & medicinal chemistry, May-01, Volume: 22, Issue:9	Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11.
AID1201060	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for chloroquine-resistant Plasmodium falciparum K1	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1858953	Antiproliferative activity against human A549 cells assessed as cell growth inhibition	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1201078	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for human A549 cells	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201076	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for human HuCCa1 cells	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1858966	Antiproliferative activity against human HepG2 cells assessed as cell growth inhibition	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
AID1201073	Cytotoxicity against human MOLT3 cells by XTT assay	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1140203	Cytotoxicity against rat L6 cells after 70 hrs by Alamar Blue assay	2014	Bioorganic & medicinal chemistry, May-01, Volume: 22, Issue:9	Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11.
AID1201075	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for human HepG2 cells	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201074	Cytotoxicity against human A549 cells by MTT assay	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201059	Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K1	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201066	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for chloroquine/mefloquine-resistant Plasmodium falciparum SRIV35	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1201063	Antiplasmodial activity against chloroquine/mefloquine-resistant Plasmodium falciparum SKF58	2015	European journal of medicinal chemistry, Apr-13, Volume: 94	Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.
AID1858960	Antimalarial activity against Plasmodium falciparum K1 infected in rat L6 cells assessed as parasite growth inhibition	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (7.69)	29.6817
2010's	8 (61.54)	24.3611
2020's	4 (30.77)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.25

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	22.25 (24.57)
Research Supply Index	2.64 (2.92)
Research Growth Index	5.59 (4.65)
Search Engine Demand Index	18.60 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (22.25)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (7.69%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	12 (92.31%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.13	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.08	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.13	1	diatomic iodine	nutrient
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.77	3	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.05	1	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
mefloquine hydrochloride [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.	2.11	1	organofluorine compound; piperidines; quinolines; secondary alcohol
thalidomide Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.	3.51	1	phthalimides; piperidones
quinoline [no description available]	2.31	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
melarsoprol Melarsoprol: Arsenical used in trypanosomiases. It may cause fatal encephalopathy and other undesirable side effects.	2.05	1	triazines
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.47	2	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.08	1	metal allergen; nickel group element atom; platinum group metal atom
benzonidazole benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.	2.05	1	C-nitro compound; imidazoles; monocarboxylic acid amide	antiprotozoal drug
etoposide [no description available]	2.11	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
ammonium peroxydisulfate ammonium persulfate : An inorganic ammonium salt in which two of the terminal hydroxy groups of peroxydisulfuric acid are deprotonated and associated with ammonium ions as counter-cations.	2.13	1
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.31	1	1,2,3-triazole
cryptolepine cryptolepine: fused indole-quinoline; structure in first source; from CRYPTOLEPIS sanguinolenta. cryptolepine : An organic heterotetracyclic compound that is 5H-indolo[3,2-b]quinoline in which the hydrogen at position N-5 is replaced by a methyl group.	3.62	2	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound	anti-inflammatory agent; antimalarial; antineoplastic agent; cysteine protease inhibitor; plant metabolite
tetrahydroharmane [no description available]	2.05	1
quindoline quindoline: a fused indole-quinoline alkaloid from CRYPTOLEPIS sanguinolenta; structure	3.51	1
gamma-carboline gamma-carboline: RN given refers to parent cpd; structure given in first source	2.31	1	pyridoindole
cryptolepine monohydrochloride [no description available]	2.05	1
4-methoxy-1-vinylcarboline [no description available]	2.05	1
neocryptolepine neocryptolepine: isolated from the roots of the African plant Cryptolepis sanguinolenta; structure in first source	3.62	2
quinine [no description available]	2.11	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	2.05	1	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.13	1	ammonium salt; inorganic sulfate salt	fertilizer
artesunate artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether	2.11	1	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
n'-(10h-indolo(3,2-b)quinolin-11-yl)-n,n-dimethylpropane-1,3-diamine [no description available]	3.51	1
amodiaquine hydrochloride [no description available]	2.1	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.51	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent

Condition	Relationship Strength	Studies
Infections, Plasmodium [description not available]	3.6	2
Benign Neoplasms [description not available]	3.33	1
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	3.6	2
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.33	1

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