Tubulin binding compounds (COBRA)
First Claim
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1. A compound of the formula whereinX is S and forms a saturated or unsaturated heterocyclic ring;
- R is a saturated or unsaturated (C7-C15) hydrocarbon chain;
R1 and R2 are independently H, (C1-C6)alkyl, (C1-C6)alkenyl, C1-C6)alkynyl, (C3-C7)cycloalkyl, aryl, or heteroaryl;
Y1 and Y2 are OH;
m is 0 to 6;
each S is independently OH, SH, CO2H, halogen, CN, acyl, thioacyl, ester, thioester, alkoxy, aryloxy, alkylthio, arylthio, alkyl, alkenyl, alkynyl, (C3-C7)cycloalkyl, aryl, heteroaryl, C(═
O)NRaRb, or NRaRb;
taken together, two of S can form a ring or any two adjacent carbons can form a double bond;
where Ra and Rb are each independently hydrogen, acyl, alkyl, (C3-C7)cycloalkyl, aryl, or heteroaryl;
or Ra and Rb together with the nitrogen to which they are attached form a ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and thiomorpholino; and
wherein R, R1, R2, Ra, and Rb are independently unsubstituted or substituted with OH, SH, CO2H, halogen, CN, acyl, thioacyl, ester, thioester, (C1-C6)alkoxy, (C1-C6)aryloxy, (C1-C6)alkylthio, (C1-C6)arylthio, (C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)alkynyl, (C3-C7)cycloalkyl, (C6-C10)aryl, or (C6-C10)heteroaryl.
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Abstract
Novel tubulin binding compounds having potent tubulin depolymerization activity and inhibitory activity against tubulin polymerization. The compounds are effective agents for inhibiting cellular proliferation, for example, in cancer cells. The compounds are adapted to interact favorably with a novel tubulin binding pocket, which pocket is useful for screening of anti-tubulin, anti-proliferation, and anti-cancer drugs.
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Citations
10 Claims
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1. A compound of the formula
wherein X is S and forms a saturated or unsaturated heterocyclic ring; -
R is a saturated or unsaturated (C7-C15) hydrocarbon chain;
R1 and R2 are independently H, (C1-C6)alkyl, (C1-C6)alkenyl, C1-C6)alkynyl, (C3-C7)cycloalkyl, aryl, or heteroaryl;
Y1 and Y2 are OH;
m is 0 to 6;
each S is independently OH, SH, CO2H, halogen, CN, acyl, thioacyl, ester, thioester, alkoxy, aryloxy, alkylthio, arylthio, alkyl, alkenyl, alkynyl, (C3-C7)cycloalkyl, aryl, heteroaryl, C(═
O)NRaRb, or NRaRb;
taken together, two of S can form a ring or any two adjacent carbons can form a double bond;
where Ra and Rb are each independently hydrogen, acyl, alkyl, (C3-C7)cycloalkyl, aryl, or heteroaryl;
or Ra and Rb together with the nitrogen to which they are attached form a ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and thiomorpholino; and
wherein R, R1, R2, Ra, and Rb are independently unsubstituted or substituted with OH, SH, CO2H, halogen, CN, acyl, thioacyl, ester, thioester, (C1-C6)alkoxy, (C1-C6)aryloxy, (C1-C6)alkylthio, (C1-C6)arylthio, (C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)alkynyl, (C3-C7)cycloalkyl, (C6-C10)aryl, or (C6-C10)heteroaryl. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
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Specification
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Current AssigneeFatih M. Uckun
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Original AssigneeParker Hughes Institute
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InventorsMao, Chen, Uckun, Fatih M., Jan, Shyi-Tai M.
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Primary Examiner(s)DENTZ, BERNARD I
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Application NumberUS09/569,314Time in Patent Office579 DaysField of Search549/78, 514/438US Class Current514/438CPC Class CodesC07C 323/41 Y being a hydrogen or an ac...C07D 307/12 Radicals substituted by oxy...C07D 307/42 Singly bound oxygen atomsC07D 493/10 Spiro-condensed systemsC07K 14/47 from mammals
