Page last updated: 2024-12-10

1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane

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

**1,1-Bis(3'-indolyl)-1-(4-hydroxyphenyl)methane** is a synthetic compound that has been shown to have promising biological activity, specifically in the context of neuroprotection and cancer therapy.

**Structure and Properties:**

* It is a triarylmethane derivative, consisting of two indole rings attached to a central carbon atom that is also linked to a 4-hydroxyphenyl group.
* The presence of the indole ring system is significant, as indole derivatives are often found in natural products and have a wide range of biological activities.
* The hydroxyl group on the phenyl ring contributes to the compound's potential for interactions with biological targets.

**Importance in Research:**

**1. Neuroprotection:**
* Studies have indicated that 1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane possesses neuroprotective properties.
* It has been shown to protect neurons from damage caused by oxidative stress, glutamate excitotoxicity, and amyloid-beta aggregation, all factors implicated in neurodegenerative diseases like Alzheimer's disease and Parkinson's disease.

**2. Cancer Therapy:**
* The compound exhibits anticancer activity against various cancer cell lines, including leukemia, breast cancer, and colon cancer.
* Its mechanism of action in cancer therapy is believed to involve inhibition of cell proliferation, induction of apoptosis (programmed cell death), and modulation of signaling pathways involved in cancer development.

**3. Other Biological Activities:**
* 1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane has also been reported to have anti-inflammatory, antioxidant, and anti-angiogenic activities.
* Its potential as a therapeutic agent for a range of diseases is being investigated.

**Current Research and Future Prospects:**

* Ongoing research focuses on understanding the precise mechanisms of action of this compound and its potential for clinical development.
* Preclinical studies are evaluating its efficacy and safety in animal models of disease.
* Further optimization of its structure and delivery methods is being investigated to improve its therapeutic potential.

**Conclusion:**

1,1-Bis(3'-indolyl)-1-(4-hydroxyphenyl)methane is a promising compound with significant potential in neuroprotection, cancer therapy, and other therapeutic areas. Its unique structural features and biological activities make it an attractive target for further research and development.

Cross-References

ID SourceID
PubMed CID2940609
CHEMBL ID1939127
SCHEMBL ID3495495
MeSH IDM0550420

Synonyms (26)

Synonym
AKOS000358286
4-[bis(1h-indol-3-yl)methyl]phenol
STK521918
4-(di-1h-indol-3-ylmethyl)phenol
CHEMBL1939127
4-(di(1h-indol-3-yl)methyl)phenol
151358-47-3
S6799
AB01248912-03
SCHEMBL3495495
dim-c-pphoh
1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane
1,1-bis(3'-indolyl)-1-(p-hydroxyphenyl)methane
phenol, 4-(di-1h-indol-3-ylmethyl)-
dim-c-pphoh(cdim8)
NCGC00340423-01
BCP28949
F21373
c-dim 8
c-dim8
mfcd03723253
DS-18778
CS-0042518
HY-112055
cdim8
A926361

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Each compound conferred significant protection against progressive loss of dopaminergic neurons in the substantia nigra pars compacta (SNpc), even when given after 7 days of dosing with MPTPp."( Novel para-phenyl substituted diindolylmethanes protect against MPTP neurotoxicity and suppress glial activation in a mouse model of Parkinson's disease.
De Miranda, BR; Hammond, SL; Miller, JA; Popichak, KA; Safe, S; Tjalkens, RB, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G-protein coupled receptor 84Homo sapiens (human)EC50 (µMol)10.00000.08903.868710.0000AID1447407; AID1447408
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
biological_processG-protein coupled receptor 84Homo sapiens (human)
neuropeptide signaling pathwayG-protein coupled receptor 84Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
urotensin II receptor activityG-protein coupled receptor 84Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneG-protein coupled receptor 84Homo sapiens (human)
specific granule membraneG-protein coupled receptor 84Homo sapiens (human)
tertiary granule membraneG-protein coupled receptor 84Homo sapiens (human)
receptor complexG-protein coupled receptor 84Homo sapiens (human)
plasma membraneG-protein coupled receptor 84Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (49)

Assay IDTitleYearJournalArticle
AID641509Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G1 phase at 2 uM after 24 hrs by flow cytometry (Rvb = 46%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641517Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G1 phase at 8 uM after 24 hrs by flow cytometry (Rvb = 65.58%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID1447406Agonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation at 10 uM after 15 mins in presence of [3H]-cAMP by radiometric assay relative to decanoic acid
AID641501Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G1 phase at 4 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641508Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G0 phase at 2 uM after 24 hrs by flow cytometry (Rvb = 2.9%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641504Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G0 phase at 8 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641497Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G1 phase at 2 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641510Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in S phase at 2 uM after 24 hrs by flow cytometry (Rvb = 14.87%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID1447425Agonist activity at human FFAR4 expressed in CHO cells assessed as beta-arrestin recruitment at 10 uM after 90 mins by beta-galactosidase complementation assay
AID641570Inhibition of HDAC1 protein expression in human MCF7 cells at 2 uM after 24 hrs by Western blotting2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641502Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in S phase at 4 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641496Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G0 phase at 2 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641571Inhibition of HDAC2 protein expression in human MCF7 cells at 2 uM after 24 hrs by Western blotting2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744541Antifungal activity against Aspergillus fumigatus ATCC 204305 by CLSI method2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID641499Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G2/M phase at 2 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744542Antibacterial activity against Mycobacterium intracellulare ATCC 23068 by alamar blue assay2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID641511Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G2/M phase at 2 uM after 24 hrs by flow cytometry (Rvb = 36.23%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641576Induction of apoptosis in human MCF7 cells assessed as caspase-7 activation at 8 uM after 24 hrs by Western blot analysis2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641569Inhibition of tubulin polymerization in human MCF7 cells at 2 uM after 24 hrs by FITC-conjugated immunostaining assay2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744540Antifungal activity against Candida albicans ATCC 90028 by CLSI method2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID1447427Antagonist activity at human FFAR4 expressed in CHO cells assessed as inhibition of TUG-89-induced beta-arrestin recruitment at 10 uM preincubated for 30 mins followed by TUG-89 addition measured after 90 mins by beta-galactosidase complementation assay
AID1447409Agonist activity at human GPR84 expressed in CHO cells assessed as beta-arrestin recruitment at 10 uM after 90 mins by beta-galactosidase complementation assay relative to embelin
AID641516Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G0 phase at 8 uM after 24 hrs by flow cytometry (Rvb = 3.22%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744548Antileishmanial activity against promastigote of Leishmania donovani after 72 hrs by alamar blue assay2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID641512Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G0 phase at 4 uM after 24 hrs by flow cytometry (Rvb = 3.22%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744544Antibacterial activity against Staphylococcus aureus ATCC 29213 by CLSI method2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID744543Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 33591 by CLSI method2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID1447413Antagonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as inhibition of decanoic acid-induced receptor activation at 10 uM
AID641572Inhibition of HDAC3 protein expression in human MCF7 cells at 2 uM after 24 hrs by Western blotting2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641506Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in S phase at 8 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744547Antileishmanial activity against axenic amastigote of Leishmania donovani after 72 hrs by alamar blue assay2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID641503Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G2/M phase at 4 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744539Antifungal activity against Cryptococcus neoformans ATCC 90113 by CLSI method2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID1447407Agonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation after 15 mins in presence of [3H]-cAMP by radiometric assay
AID641500Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G0 phase at 4 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641514Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in S phase at 4 uM after 24 hrs by flow cytometry (Rvb = 5.55%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641498Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in S phase at 2 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641495Anticancer activity against human MCF7 cells assessed as cell death at 2 uM after 24 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641507Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G2/M phase at 8 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641519Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G2/M phase at 8 uM after 24 hrs by flow cytometry (Rvb = 25.65%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641573Inhibition of HDAC8 protein expression in human MCF7 cells at 2 uM after 24 hrs by Western blotting2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641575Induction of apoptosis in human MCF7 cells assessed as PARP-cleavage at 8 uM after 24 hrs by Western blot analysis2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID744545Cytotoxicity against african green monkey Vero cells up to 4.6 ug/ml after 48 hrs by neutral red assay2013European journal of medicinal chemistry, May, Volume: 63Discovery of 3,3'-diindolylmethanes as potent antileishmanial agents.
AID1447424Agonist activity at Gq protein coupled human FFAR1 expressed in human 1321N1 cells assessed as induction of intracellular calcium level at 10 uM measured at 1.2 secs time interval by Fluo-4-AM dye based fluorescence assay
AID641513Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G1 phase at 4 uM after 24 hrs by flow cytometry (Rvb = 65.58%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID1447408Agonist activity at human GPR84 expressed in CHO cells assessed as beta-arrestin recruitment after 90 mins by beta-galactosidase complementation assay
AID641518Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in S phase at 8 uM after 24 hrs by flow cytometry (Rvb = 5.55%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641505Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G1 phase at 8 uM after 24 hrs by flow cytometry relative to untreated control2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
AID641515Induction of cell cycle arrest in human MCF7 cells assessed as accumulation of cells in G2/M phase at 4 uM after 24 hrs by flow cytometry (Rvb = 25.65%)2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's17 (94.44)24.3611
2020's1 (5.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.14

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.14 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index6.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.56%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]