Cyclobut A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 412314

CAS#: 124770-85-0

Description: Cyclobut A is a biochemical

Chemical Structure

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Cyclobut A
CAS# 124770-85-0
Instruction

Theoretical Analysis

MedKoo Cat#: 412314
Name: Cyclobut A
CAS#: 124770-85-0
Chemical Formula: C11H15N5O2
Exact Mass: 249.12
Molecular Weight: 249.270
Elemental Analysis: C, 53.00; H, 6.07; N, 28.10; O, 12.84

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Cyclobut A; COxt-A; C Oxt-A; C-Oxt-A

IUPAC/Chemical Name: 1,2-Cyclobutanedimethanol, 3-(6-amino-9H-purin-9-yl)-, (1alpha,2beta,3alpha)-(+-)-

InChi Key: PYJIWOQTJHPDAK-BWZBUEFSSA-N

InChi Code: InChI=1S/C11H15N5O2/c12-10-9-11(14-4-13-10)16(5-15-9)8-1-6(2-17)7(8)3-18/h4-8,17-18H,1-3H2,(H2,12,13,14)/t6-,7-,8-/m1/s1

SMILES Code: OC[C@@H]1[C@@H](CO)[C@H](N2C=NC3=C(N)N=CN=C23)C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 249.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hayashi S, Norbeck DW, Rosenbrook W, Fine RL, Matsukura M, Plattner JJ, Broder S, Mitsuya H. Cyclobut-A and cyclobut-G, carbocyclic oxetanocin analogs that inhibit the replication of human immunodeficiency virus in T cells and monocytes and macrophages in vitro. Antimicrob Agents Chemother. 1990 Feb;34(2):287-94. doi: 10.1128/aac.34.2.287. PMID: 2327778; PMCID: PMC171575.

2: Yang Y, Petersen JL, Wang KK. Cascade radical cyclizations of benzannulated enyne-allenes. Unusual cleavage of a benzene ring leading to twisted 1,1'-dialkyl-9,9'-bifluorenylidenes and spiro[1H-cyclobut[a]indene-1,9'-[9H]fluorenes]. J Org Chem. 2003 Jul 25;68(15):5832-7. doi: 10.1021/jo030147j. PMID: 12868915.

3: Rao SN. Conformations of Cyclobut-A and Cyclobut-G: structural resemblance to nucleosides and incorporation into double helical DNA. J Biomol Struct Dyn. 1992 Feb;9(4):719-32. doi: 10.1080/07391102.1992.10507951. PMID: 1616627.

4: Li H, Zhang HR, Petersen JL, Wang KK. Biradicals from benzoenyne-allenes. Application in the synthesis of 11H-benzo[b]fluoren-11-ols, 1H-cyclobut[a]indenes, and related compounds. J Org Chem. 2001 Oct 5;66(20):6662-8. doi: 10.1021/jo0104577. PMID: 11578218.

5: Norbeck DW, Kern E, Hayashi S, Rosenbrook W, Sham H, Herrin T, Plattner JJ, Erickson J, Clement J, Swanson R, et al. Cyclobut-A and cyclobut-G: broad- spectrum antiviral agents with potential utility for the therapy of AIDS. J Med Chem. 1990 May;33(5):1281-5. doi: 10.1021/jm00167a002. PMID: 2329551.

6: Kulikowski T. Structure-activity relationships and conformational features of antiherpetic pyrimidine and purine nucleoside analogues. A review. Pharm World Sci. 1994 Apr 15;16(2):127-38. doi: 10.1007/BF01880663. PMID: 8032338.

7: Hung LF, Brumbaugh AE, Bhatia G, Marion PL, Hung PP, Norbeck DW, Plattner JJ, Robinson WS. Effects of purine nucleoside analogues with a cyclobutane ring and erythromycin A oxime derivatives on duck hepatitis B virus replication in vivo and in cell culture and HIV-1 in cell culture. J Med Virol. 1991 Nov;35(3):180-6. doi: 10.1002/jmv.1890350307. PMID: 1804929.

8: Rustullet A, Alibés R, de March P, Figueredo M, Font J. Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone. Org Lett. 2007 Jul 19;9(15):2827-30. doi: 10.1021/ol0710616. Epub 2007 Jun 21. PMID: 17583347.

9: Yang Y, Petersen JL, Wang KK. Polycyclic aromatic compounds via radical cyclizations of benzannulated enyne-allenes derived from Ireland-Claisen rearrangement. J Org Chem. 2003 Oct 31;68(22):8545-9. doi: 10.1021/jo035036z. PMID: 14575484.

10: Maruyama T, Hanai Y, Sato Y, Snoeck R, Andrei G, Hosoya M, Balzarini J, De Clercq E. Synthesis and antiviral activity of carbocyclic oxetanocin analogues (C-OXT-A, C-OXT-G) and related compounds. II. Chem Pharm Bull (Tokyo). 1993 Mar;41(3):516-21. doi: 10.1248/cpb.41.516. PMID: 8386594.