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59787-61-0

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59787-61-0 Usage

Description

Cyclosporin C is a fungal metabolite that has been found in T. inflatum and has diverse biological activities, including antifungal, antiviral, and immunosuppressant properties. It is active against isolates of B. cinerea, A. niger, and Alternaria, Mucor, and Penicillium species (MICs = 0.1-5 μg/ml). Cyclosporin C (15 μg/ml) inhibits vaccinia virus replication in infected BSC40 cells by 98.82%. It inhibits lymphocyte proliferation induced by the mitogens concanavalin A (ConA; ), phytohemagglutinin L (PHA), and pokeweed mitogen (PWM), as well as proliferation induced by alloantigen in mixed lymphocyte culture when used at a concentration of 100 ng/ml. Cyclosporin C (100 ng/ml) inhibits the local graft versus host (GVH) reaction in mice receiving splenocyte grafts.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 59787-61-0 differently. You can refer to the following data:
1. A group of nonpolar cyclic oligopeptides with immunosupppressant activity.
2. Cyclosporin C is a minor analogue of the cyclosporin complex produced by a number of fungal species, including Trichoderma, Tolypocladium, Fusarium, Nectria and Acremonium. Cyclosporin C possesses immunosuppressant activity but has been much less extensively investigated than the major analogue, cyclosporin A.

Check Digit Verification of cas no

The CAS Registry Mumber 59787-61-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,7,8 and 7 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 59787-61:
(7*5)+(6*9)+(5*7)+(4*8)+(3*7)+(2*6)+(1*1)=190
190 % 10 = 0
So 59787-61-0 is a valid CAS Registry Number.
InChI:InChI=1/C62H111N11O13/c1-25-26-27-39(14)52(76)51-56(80)66-49(42(17)74)60(84)67(18)32-47(75)68(19)43(28-33(2)3)55(79)65-48(37(10)11)61(85)69(20)44(29-34(4)5)54(78)63-40(15)53(77)64-41(16)57(81)70(21)45(30-35(6)7)58(82)71(22)46(31-36(8)9)59(83)72(23)50(38(12)13)62(86)73(51)24/h25-26,33-46,48-52,74,76H,27-32H2,1-24H3,(H,63,78)(H,64,77)(H,65,79)(H,66,80)/b26-25+/t39-,40+,41-,42-,43+,44+,45+,46+,48+,49+,50+,51+,52-/m1/s1

59787-61-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclosporin C

1.2 Other means of identification

Product number -
Other names 7-L-Threoninecyclosporin A

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59787-61-0 SDS

59787-61-0Synthetic route

C70H117N11O14

C70H117N11O14

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 300h; pH=1; Kinetics;100%
cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

4-dimethoxymethyl-benzoic acid allyl ester

4-dimethoxymethyl-benzoic acid allyl ester

C73H119N11O15

C73H119N11O15

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene for 0.833333h; Heating;95%
biphenyl-4-carboxaldehyde dimethyl acetal
126651-12-5

biphenyl-4-carboxaldehyde dimethyl acetal

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C75H119N11O13

C75H119N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene for 0.5h; Heating;89%
3,3-dimethoxyprop-1-ene
6044-68-4

3,3-dimethoxyprop-1-ene

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C65H113N11O13

C65H113N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene for 1h; Heating;75%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C69H115N11O13

C69H115N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene for 0.75h; Heating;74%
methyl 4-(dimethoxymethyl)benzoate
42228-16-0

methyl 4-(dimethoxymethyl)benzoate

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C71H117N11O15

C71H117N11O15

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene for 2h; Heating;55%
1,1-dimethoxybutane
4461-87-4

1,1-dimethoxybutane

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C66H117N11O13

C66H117N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 100 - 120℃; for 16h;39%
dimethoxypropane
4744-10-9

dimethoxypropane

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C65H115N11O13

C65H115N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 100 - 120℃; for 16h;34%
1,1-dimethoxyethane
534-15-6

1,1-dimethoxyethane

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C64H113N11O13

C64H113N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 100 - 120℃; for 16h;33%
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C65H115N11O13

C65H115N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 100 - 120℃; for 16h;26%
3,3-dimethoxypentane
25636-49-1

3,3-dimethoxypentane

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

C67H119N11O13

C67H119N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 100 - 120℃; for 16h;22%
cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]
59787-61-0

cyclo-[MeBmt-Thr-Sar-MeLeu-Val-MeLeu-Ala-D-Ala-MeLeu-MeLeu-MeVal]

isobutyraldehyde dimethyl acetal
41632-89-7

isobutyraldehyde dimethyl acetal

C66H117N11O13

C66H117N11O13

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 100 - 120℃; for 16h;19%

59787-61-0Upstream product

59787-61-0Downstream Products

59787-61-0Relevant articles and documents

Pseudoprolines (psiPro) in drug design: direct insertion of psiPro systems into cyclosporin C.

Keller,Woehr,Dumy,Patiny,Mutter

, p. 4358 - 4363 (2007/10/03)

The insertion of acetals that exhibit variable structural features into complex peptides such as cyclosporin C (CsC) results in oxazolidine derivatives (pseudoprolines, psiPro) of tailored physico-chemical and biological properties. N,O-Acetalation of the 2-threonine hydroxyl group and the preceding amide nitrogen of CsC is achieved by treating the molecule with a number of both arylated and non-arylated dimethyl acetals. The psiPro-containing CsC derivatives exhibit enhanced conformational backbone rigidity, as suggested by analytical HPLC, NMR spectroscopy and by kinetic measurements on binding with their receptor protein cyclophilin A (CypA) that were not time-dependent. IC50 values for calf-thymus CypA were obtained by kinetic evaluation of its cis-->trans isomerase activity. The choice of the para-substituted aryl dimethyl acetals allows the inhibitory properties of the corresponding derivatives to be modulated to either prodrugs or moderately strongly binding cyclosporin C derivatives.

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