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Home > Other Heterocycles > 158440-71-2
158440-71-2 | Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (6'R)-
CAS No: 158440-71-2 Catalog No: AG001Q6R MDL No:
Product Description
Catalog Number:
AG001Q6R
Chemical Name:
Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (6'R)-
CAS Number:
158440-71-2
Molecular Formula:
C15H18O3
Molecular Weight:
246.3016
IUPAC Name:
(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
InChI:
InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
InChI Key:
NICJCIQSJJKZAH-AWEZNQCLSA-N
SMILES:
OCC1=C(C)C=C2C1=C(C)C1([C@@](C2=O)(C)O)CC1
UNII:
6B799IH05A
NSC Number:
683863
Properties
Complexity:
558
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
246.126g/mol
Formal Charge:
0
Heavy Atom Count:
18
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
246.306g/mol
Monoisotopic Mass:
246.126g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
57.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.2
Literature
| Title | Journal |
|---|---|
| Modulation of Cytotoxicity by Transcription-Coupled Nucleotide Excision Repair Is Independent of the Requirement for Bioactivation of Acylfulvene. | Chemical research in toxicology 20170320 |
| Sulfotransferase-independent genotoxicity of illudin S and its acylfulvene derivatives in bacterial and mammalian cells. | Archives of toxicology 20140101 |
| Up-regulation of human prostaglandin reductase 1 improves the efficacy of hydroxymethylacylfulvene, an antitumor chemotherapeutic agent. | The Journal of pharmacology and experimental therapeutics 20121101 |
| Pharmacokinetic modeling of an induction regimen for in vivo combined testing of novel drugs against pediatric acute lymphoblastic leukemia xenografts. | PloS one 20120101 |
| Cytotoxicity and genotoxicity of capecitabine in head and neck cancer and normal cells. | Molecular biology reports 20110801 |
| Strand-specific PCR of UV radiation-damaged genomic DNA revealed an essential role of DNA-PKcs in the transcription-coupled repair. | BMC biochemistry 20110101 |
| Enhanced anticancer activity of gemcitabine in combination with noscapine via antiangiogenic and apoptotic pathway against non-small cell lung cancer. | PloS one 20110101 |
| A phase 2 evaluation of irofulven as second-line treatment of recurrent or persistent intermediately platinum-sensitive ovarian or primary peritoneal cancer: a Gynecologic Oncology Group trial. | International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20101001 |
| A ubiquitin-binding domain in Cockayne syndrome B required for transcription-coupled nucleotide excision repair. | Molecular cell 20100611 |
| Structure-activity studies of urea, carbamate, and sulfonamide derivatives of acylfulvene. | Journal of medicinal chemistry 20100211 |
| Dissociation of CAK from core TFIIH reveals a functional link between XP-G/CS and the TFIIH disassembly state. | PloS one 20100101 |
| Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven. | The Journal of organic chemistry 20091218 |
| Profiling patterns of glutathione reductase inhibition by the natural product illudin S and its acylfulvene analogues. | Molecular bioSystems 20090901 |
| Synergy of irofulven in combination with other DNA damaging agents: synergistic interaction with altretamine, alkylating, and platinum-derived agents in the MV522 lung tumor model. | Cancer chemotherapy and pharmacology 20081201 |
| Combination chemotherapy and photodynamic therapy with fab' fragment targeted HPMA copolymer conjugates in human ovarian carcinoma cells. | Molecular pharmaceutics 20081006 |
| Synergy of Irofulven in combination with various anti-metabolites, enzyme inhibitors, and miscellaneous agents in MV522 lung carcinoma cells: marked interaction with gemcitabine and 5-fluorouracil. | Investigational new drugs 20081001 |
| Conjugates of the fungal cytotoxin illudin M with improved tumour specificity. | Bioorganic & medicinal chemistry 20080915 |
| The development of xenograft glioblastoma implants in nude mice brain. | Journal of medicine and life 20080815 |
| Ovarian tumor growth regression using a combination of vascular targeting agents anginex or topomimetic 0118 and the chemotherapeutic irofulven. | Cancer letters 20080708 |
| The postchemotherapy PSA surge syndrome. | Annals of oncology : official journal of the European Society for Medical Oncology 20080701 |
| Influence of irofulven, a transcription-coupled repair-specific antitumor agent, on RNA polymerase activity, stability and dynamics in living mammalian cells. | Journal of cell science 20080415 |
| Systematic review of the clinical effect of glucocorticoids on nonhematologic malignancy. | BMC cancer 20080101 |
| Synthesis and antitumor activity of amine analogs of irofulven. | Bioorganic & medicinal chemistry letters 20071215 |
| A phase I and pharmacokinetic study of irofulven and capecitabine administered every 2 weeks in patients with advanced solid tumors. | Investigational new drugs 20071001 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20070601 |
| BRCA1 contributes to cell cycle arrest and chemoresistance in response to the anticancer agent irofulven. | Molecular pharmacology 20070401 |
| Irofulven induces replication-dependent CHK2 activation related to p53 status. | Biochemical pharmacology 20070215 |
| Irofulven as first line therapy in recurrent or metastatic gastric cancer: a phase II multicenter study by the Cancer Therapeutics Research Group (CTRG). | Cancer chemotherapy and pharmacology 20070201 |
| Comparison of antitumor activities in tumor xenograft treatment. | Contemporary clinical trials 20070201 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20070101 |
| Fanconi anemia D2 protein confers chemoresistance in response to the anticancer agent, irofulven. | Molecular cancer therapeutics 20061201 |
| Pharmacokinetics, metabolism, and routes of excretion of intravenous irofulven in patients with advanced solid tumors. | Drug metabolism and disposition: the biological fate of chemicals 20061101 |
| Rescue of progeria in trichothiodystrophy by homozygous lethal Xpd alleles. | PLoS biology 20061001 |
| Phase I trial of irofulven (MGI 114) in pediatric patients with solid tumors. | Pediatric blood & cancer 20060801 |
| A phase I and pharmacokinetic study of irofulven and cisplatin administered in a 30-min infusion every two weeks to patients with advanced solid tumors. | Investigational new drugs 20060701 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20060601 |
| Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity. | Journal of medicinal chemistry 20060420 |
| Characterizations of irofulven cytotoxicity in combination with cisplatin and oxaliplatin in human colon, breast, and ovarian cancer cells. | Cancer chemotherapy and pharmacology 20060401 |
| A phase II study of irofulven in women with recurrent and heavily pretreated ovarian cancer. | Gynecologic oncology 20060401 |
| Non-hormonal systemic therapy in men with hormone-refractory prostate cancer and metastases: a systematic review from the Cancer Care Ontario Program in Evidence-based Care's Genitourinary Cancer Disease Site Group. | BMC cancer 20060101 |
| Pharmacokinetic modelling of 5-FU production from capecitabine--a population study in 40 adult patients with metastatic cancer. | Journal of pharmacokinetics and pharmacodynamics 20051201 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20050901 |
| Enhanced antitumor activity of irofulven in combination with irinotecan in pediatric solid tumor xenograft models. | Cancer chemotherapy and pharmacology 20050501 |
| Irofulven demonstrates clinical activity against metastatic hormone-refractory prostate cancer in a phase 2 single-agent trial. | American journal of clinical oncology 20050201 |
| Cone damage in patients receiving high-dose irofulven treatment. | Archives of ophthalmology (Chicago, Ill. : 1960) 20050101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20041201 |
| Characterization and multiparameter analysis of visual adverse events in irofulven single-agent phase I and II trials. | Clinical cancer research : an official journal of the American Association for Cancer Research 20041115 |
| Cell cycle effects and induction of premitotic apoptosis by irofulven in synchronized cancer cells. | Cancer biology & therapy 20041101 |
| Caspase-mediated apoptosis and caspase-independent cell death induced by irofulven in prostate cancer cells. | Molecular cancer therapeutics 20041101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20041101 |
| Irofulven: resurgence for alkylating therapy in cancer? | Cancer biology & therapy 20041101 |
| ATM-dependent CHK2 activation induced by anticancer agent, irofulven. | The Journal of biological chemistry 20040917 |
| A phase II trial of 6-hydroxymethylacylfulvene (MGI-114, irofulven) in patients with relapsed or refractory non-small cell lung cancer. | Lung cancer (Amsterdam, Netherlands) 20040901 |
| Irofulven cytotoxicity depends on transcription-coupled nucleotide excision repair and is correlated with XPG expression in solid tumor cells. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040815 |
| Evaluation of irofulven (MGI-114) in the treatment of recurrent or persistent endometrial carcinoma: A phase II study of the Gynecologic Oncology Group. | Investigational new drugs 20040801 |
| Phase I and pharmacokinetic study of irofulven administered weekly or biweekly in advanced solid tumor patients. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040515 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20040501 |
| Acute retinal toxicity from the novel anti-tumor agent, Irofulven. | Documenta ophthalmologica. Advances in ophthalmology 20040501 |
| Antitumor activity of irofulven monotherapy and in combination with mitoxantrone or docetaxel against human prostate cancer models. | The Prostate 20040401 |
| NADPH alkenal/one oxidoreductase activity determines sensitivity of cancer cells to the chemotherapeutic alkylating agent irofulven. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040215 |
| Synthesis and biological activity of enantiomers of antitumor irofulven. | The Journal of organic chemistry 20040206 |
| Activity of irofulven against human pancreatic carcinoma cell lines in vitro and in vivo. | Anticancer research 20040101 |
| Antitumor activity of irofulven against human ovarian cancer cell lines, human tumor colony-forming units, and xenografts. | International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20040101 |
| Enhanced antitumor activity of irofulven in combination with 5-fluorouracil and cisplatin in human colon and ovarian carcinoma cells. | International journal of oncology 20031101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20031101 |
| Advanced pancreatic cancer: is there a role for combination therapy? | Expert review of anticancer therapy 20031001 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20030901 |
| Marked activity of irofulven toward human carcinoma cells: comparison with cisplatin and ecteinascidin. | Clinical cancer research : an official journal of the American Association for Cancer Research 20030701 |
| Phase I population pharmacokinetics of irofulven. | Anti-cancer drugs 20030601 |
| Irinotecan plus raltitrexed vs raltitrexed alone in patients with gemcitabine-pretreated advanced pancreatic adenocarcinoma. | British journal of cancer 20030422 |
| Phase II study of MGI-114 administered intravenously for 5 days every 28 days to patients with metastatic colorectal cancer. | American journal of clinical oncology 20030401 |
| Gateways to clinical trials. March 2003. | Methods and findings in experimental and clinical pharmacology 20030301 |
| Apoptosis induction by the dual-action DNA- and protein-reactive antitumor drug irofulven is largely Bcl-2-independent. | Biochemical pharmacology 20030215 |
| Reaction of irofulven with zinc and acid. | Journal of natural products 20030201 |
| [Perspectives on the oncologist pharmacopoeia]. | Bulletin du cancer 20030101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20030101 |
| Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways. | DNA repair 20021205 |
| Irofulven, a novel inhibitor of DNA synthesis, in metastatic renal cell cancer. | Investigational new drugs 20021101 |
| Irofulven (MGI Pharma). | Current opinion in investigational drugs (London, England : 2000) 20021001 |
| Relation between Irofulven (MGI-114) systemic exposure and tumor response in human solid tumor xenografts. | Clinical cancer research : an official journal of the American Association for Cancer Research 20020901 |
| Enhanced antitumor activity of irofulven in combination with antimitotic agents. | Investigational new drugs 20020801 |
| A phase II study of Irofulven (MGI 114) in patients with stage IV melanoma. | Investigational new drugs 20020801 |
| Preferential targeting of apoptosis in tumor versus normal cells. | Biochimica et biophysica acta 20020718 |
| Enhanced antitumor activity of irofulven in combination with thiotepa or mitomycin C. | Cancer chemotherapy and pharmacology 20020501 |
| Irofulven induces apoptosis in breast cancer cells regardless of caspase-3 status. | Breast cancer research and treatment 20020101 |
| Irofulven (6-hydroxymethylacylfulvene, MGI 114)-induced apoptosis in human pancreatic cancer cells is mediated by ERK and JNK kinases. | Anticancer research 20020101 |
| Phase I clinical and pharmacokinetic trial of irofulven. | Cancer chemotherapy and pharmacology 20011201 |
| Activity of irofulven (6-hydroxymethylacylfulvene) in the treatment of glioblastoma multiforme-derived xenografts in athymic mice. | Cancer chemotherapy and pharmacology 20011101 |
| Structure-activity studies of antitumor agent irofulven (hydroxymethylacylfulvene) and analogues. | The Journal of organic chemistry 20010907 |
| In vivo antitumour efficacy of MGI-114 (6-hydroxymethylacylfulvene, HMAF) in various human tumour xenograft models including several lung and gastric tumours. | European journal of cancer (Oxford, England : 1990) 20010701 |
| Phase I study of irofulven (MGI 114), an acylfulvene illudin analog, in patients with acute leukemia. | Investigational new drugs 20010101 |
| A phase II trial of 6-hydroxymethylacylfulvene (MGI-114, irofulven) in patients with advanced non-small cell cancer previously treated with chemotherapy. | Investigational new drugs 20010101 |
| Irofulven (6-hydroxymethylacylfulvene, MGI 114) induces caspase 8 and 9-mediated apoptosis in human pancreatic adenocarcinoma cells. | Anticancer research 20010101 |
| Changes in prostate-specific antigen (PSA) level correlate with growth inhibition of prostate cancer cells treated in vitro with a novel anticancer drug, irofulven. | Investigational new drugs 20010101 |
| Phase II trial of irofulven (6-hydroxymethylacylfulvene) for patients with advanced renal cell carcinoma. | Investigational new drugs 20010101 |
| DNA: still a target worth aiming at? A review of new DNA-interactive agents. | American journal of pharmacogenomics : genomics-related research in drug development and clinical practice 20010101 |
| Anti-leukemic action of the novel agent MGI 114 (HMAF) and synergistic action with topotecan. | Leukemia 20000101 |
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