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12,13-二氢-5H-吲哚并[2,3-a]吡咯并[3,4-C]咔唑-5,7(6H)-二酮 | 118458-54-1

分子结构分类

有机化合物 - 有机杂环化合物 - 吲哚及其衍生物

中文名称

12,13-二氢-5H-吲哚并[2,3-a]吡咯并[3,4-C]咔唑-5,7(6H)-二酮

中文别名

——

英文名称

arcyriaflavin A

英文别名

12,13-dihydro-5H-indolo [2,3-a] pyrrolo[3,4-c] carbazole-5,7(6H)-dione；12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione；indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione；7-oxostaurosporine；arcyriaflavin-A.；3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione

12,13-二氢-5H-吲哚并[2,3-a]吡咯并[3,4-C]咔唑-5,7(6H)-二酮化学式

CAS

118458-54-1

化学式

C₂₀H₁₁N₃O₂

mdl

——

分子量

325.326

InChiKey

KAJXOWFGKYKMMZ-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

>200 °C
密度：

1.621±0.06 g/cm3(Predicted)
溶解度：

溶于二甲基亚砜

计算性质

辛醇/水分配系数(LogP)：

3.6
重原子数：

25
可旋转键数：

0
环数：

6.0
sp3杂化的碳原子比例：

0.0
拓扑面积：

77.8
氢给体数：

3
氢受体数：

2

安全信息

储存条件：

-20°C下存储在惰性气体中，避免与空气接触并防止加热。

SDS

SDS：c38c07716c8c61955c56b645a5b7bc7f

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制备方法与用途

Arcyriaflavin A是从诺卡菌属真菌中获得的一种真菌代谢产物。

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	6,7,12,13-tetrahydro-5,7-dioxo-5H-indolo<2,3-a>furo<3,4-c>carbazole	115684-58-7	C₂₀H₁₀N₂O₃	326.311
——	4-(2'-Nitrophenyl)-2,3-dihydro-2H,6H-pyrrolo<3,4-c>carbazol-1,3-dione	128287-91-2	C₂₀H₁₁N₃O₄	357.325

下游产品

中文名称	英文名称	CAS号	化学式	分子量
6,7,12,13-四氢-5H-吲哚并[2,3-a]吡咯并[3,4-c]咔唑-5-酮	staurosporine aglycone	85753-43-1	C₂₀H₁₃N₃O	311.343
——	12,13-dihydro-3,9-dibromo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione	118458-61-0	C₂₀H₉Br₂N₃O₂	483.118
——	tjipanazole L	118458-60-9	C₂₀H₉Cl₂N₃O₂	394.216
——	19-(3-Methylbut-2-enyl)-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17(22),18,20-nonaen-12-one	1412453-32-7	C₂₅H₂₁N₃O	379.461
——	7-(3-Methylbut-2-enyl)-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17,19,21-nonaen-12-one	1412453-31-6	C₂₅H₂₁N₃O	379.461
——	7,19-Bis(3-methylbut-2-enyl)-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaen-12-one	1412453-33-8	C₃₀H₂₉N₃O	447.58
——	7-hydroxy-K252c	——	C₂₀H₁₃N₃O₂	327.342
——	12-ethyl-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5,7(6H)-dione	——	C₂₂H₁₅N₃O₂	353.38
——	didemethylreductasporine	——	C₂₀H₁₅N₃	297.359
——	12-(N-propylamino)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione	177330-16-4	C₂₃H₁₈N₄O₂	382.422
——	12-Benzylindolo[2,3-a]3-pyrrolino[3,4-c]carbazole-5,7-dione	——	C₂₇H₁₇N₃O₂	415.451
——	12,13-di-(4-butenyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	956288-11-2	C₂₈H₂₅N₃O	419.526
——	12,13-[1,4-but-(cis-2-en)-diyl]-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₄H₁₇N₃O	363.418
——	12,13-di-[1,6-hex-(cis-3-en)-diyl]-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₆H₂₁N₃O	391.472
——	12,13-(2-methylene-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	928629-53-2	C₂₄H₁₇N₃O	363.418
——	12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	928629-55-4	C₂₄H₁₉N₃O₂	381.434
——	12,13-(2,2-bis-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₅H₂₁N₃O₃	411.46
——	12,13-[(2R,3R)-dihydroxy-butan-1,4-yl]-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₄H₁₉N₃O₃	397.433
——	9-hydroxymethyl-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₅H₂₁N₃O₃	411.46
——	3,9-bis-(hydroxymethyl)-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	928629-70-3	C₂₆H₂₃N₃O₄	441.486
——	12,13-(2-hydroxy-2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₄H₁₉N₃O₃	397.433
——	3,9-bis-(isopropoxymethyl)-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₃₂H₃₅N₃O₄	525.648
——	3-[(2E)-2-carboxy-ethenyl]-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₇H₂₁N₃O₄	451.481
——	3-bromo-9-formyl-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₅H₁₈BrN₃O₃	488.34
——	12,13-{2-[(5-spiro)-(2,2-dimethyl-[1,3]dioxan-5-yl)]-propan-1,3-yl}-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	928629-82-7	C₂₈H₂₅N₃O₃	451.525
——	12,13-diallyl-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-carboxylic acid tert-butyl ester	——	C₃₁H₂₉N₃O₃	491.59
——	3-{(1E)-3-[(4,5-dihydro-1H-imidazol-2-yl)amino]-prop-1-en-1-yl}-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₃₀H₂₈N₆O₂	504.591
——	3-bromo-9-(morpholin-4-ylmethyl)-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₉H₂₇BrN₄O₃	559.462
——	3-[(1E)-3-1H-imidazol-1-yl-prop-1-en-1-yl]-9-hydroxymethyl-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₃₁H₂₇N₅O₃	517.587
——	12,13-(but-2-en-1,4-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-carboxylic acid tert-butyl ester	——	C₂₉H₂₅N₃O₃	463.536
9,10,11,12-四氢-9,12-环氧-1H-二吲哚[1,2,3-fg：3'，2'，1'-kl]吡咯并[3,4-i][1，6]苯并重氮电影-1,3(2H)-二酮	9,10,11,12-tetrahydro-9,12-epoxy-1H-diindolo[1,2,3-fg:3′,2′,1′-kl]pyrrolo[3,4-i][1,6] benzodiazocine-1,3(2H)-dione	135897-06-2	C₂₄H₁₅N₃O₃	393.401
——	6-t-butoxycarbonyl-12,13-di-(4-butenyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₃₃H₃₃N₃O₃	519.643
——	3-bromo-9-(isopropoxymethyl)-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₈H₂₆BrN₃O₃	532.437
——	6-t-butoxycarbonyl-12,13-(1,6-hex-cis-3-enyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₃₁H₂₉N₃O₃	491.59
——	12,13-[(4R,5R)-2,2-dimethyl-[1,3]dioxolo[4,5-b]butan-1,4-yl]-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₂₇H₂₃N₃O₃	437.498
——	3-[(2E)-2-(4-methyl-thiazol-5-yl)ethenyl]-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole	——	C₃₀H₂₄N₄O₂S	504.612
——	12,13-(2,3-dihydroxy-butan-1,4-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-carboxylic acid tert-butyl ester	953398-22-6	C₂₉H₂₇N₃O₅	497.55

反应信息

作为反应物：

描述：

12,13-二氢-5H-吲哚并[2,3-a]吡咯并[3,4-C]咔唑-5,7(6H)-二酮在 palladium on activated charcoal lithium aluminium tetrahydride 、氢气作用下，以乙醚、乙醇为溶剂，生成 6,7,12,13-四氢-5H-吲哚并[2,3-a]吡咯并[3,4-c]咔唑-5-酮

参考文献：

名称：

用乙酸钯进行氧化环化。星形孢菌素糖苷配基的短合成。

摘要：

乙酸钯介导的氧化环化已被用作合成星形孢菌素糖苷配基和相关类似物的关键步骤。

DOI：

10.1016/s0040-4039(00)61431-4
作为产物：

描述：

1-苄基-1H-吲哚-2-甲醛在 sodium cyanide 、 manganese(IV) oxide 、 aluminum (III) chloride 、 potassium tert-butylate 、 sodium hydride 、溶剂黄146 、三氟乙酸作用下，以二氯甲烷、 N,N-二甲基甲酰胺、甲苯、 mineral oil 为溶剂，反应 4.5h，生成 12,13-二氢-5H-吲哚并[2,3-a]吡咯并[3,4-C]咔唑-5,7(6H)-二酮

参考文献：

名称：

以2,2'-双吲哚-3-乙酸衍生物为常见中间体，合成迷迭香黄素A和Calothrixin B

摘要：

通过氰化物催化的亚氨基-Stetter反应，开发了一种由2-氨基肉桂酸衍生物和吲哚-2-羧醛衍生的亚胺合成2,2'-双吲哚-3-乙酸衍生物的新方法。通过该方案，使用2,2'-双吲哚-3-乙酸完成了代表性的吲哚并咔唑天然产物arcyriaflavin A和代表性的吲哚[3,2- j ]菲啶天然产物calothrixin B的不同总合成。酸衍生物为常见中间体。

DOI：

10.1021/acs.orglett.7b00687

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文献信息

A facile synthesis of staurosporine aglycone

作者：Guojian Xie、J. William Lown

DOI：10.1016/s0040-4039(00)77245-5

日期：1994.8

A highly efficient method is described for the synthesis of staurosporine aglycone 3 from the readily available dibromomaleic acid in six steps.

描述了一种高效的方法，该方法可通过六个步骤从容易获得的二溴马来酸合成星形孢菌素苷元3。
Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A

作者：Jan Bergman、Eva Koch、Benjamin Pelcman

DOI：10.1039/b004029k

日期：——

The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promoted coupling of the dianion 9. The diester was converted to the N-benzylimide 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carbazole 15. The diester 10 could be directly transformed to the known indolocarbazole diester 27via acid-induced intramolecular cyclization in TFA. The same methodology gave arcyriaflavin A 4 from the succinimide 18b.

双吲哚基琥珀酸甲酯10是通过碘促进的双阴离子9的耦合反应获得的。该二酯被转化为N-苄基亚胺12，随后经过氧化环合得到吲哚[2,3-a]吡咯[3,4-c]咔唑15。二酯10可以直接通过三氟乙酸中的酸诱导分子内环合反应转化为已知的吲哚咔唑二酯27。同样的合成方法从琥珀酰亚胺18b得到了亮菌素A 4。
The synthesis of bioactive indolocarbazoles related to K-252a

作者：David Moffat、Christopher J. Nichols、Dean A. Riley、Nigel S. Simpkins

DOI：10.1039/b506444a

日期：——

n to give a ketone, or by dihydroxylation and cyclic sulfate formation, enable the preparation of diverse indolocarbazole products. Issues of imide nitrogen protection for the indolocarbazole, and opportunities for asymmetric desymmetrisation of key intermediates were also explored. A novel chiral lithium amide base mediated transformation of a cyclic sulfate intermediate gave the anticipated ketone

从容易获得的桥连环戊烯开始，已制备了一系列与天然产物K-252a有关的功能化吲哚并咔唑。涉及初始氢硼化-氧化以生成酮的转化序列，或通过二羟基化和环状硫酸盐形成的转化序列，使得能够制备各种吲哚并咔唑产物。还探讨了吲哚并咔唑的酰亚胺氮保护问题以及关键中间体的不对称脱对称现象。新型的手性锂酰胺基碱介导的环状硫酸盐中间体的转化产生了预期的酮产物，其收率高达87％ee。筛选了未保护的酰亚胺取代的吲哚并咔唑形式的许多化合物的生物活性，发现它们是多种激酶的有效抑制剂。
Synthetic staurosporines via a ring closing metathesis strategy as potent JAK3 inhibitors and modulators of allergic responses

作者：Lawrence J. Wilson、Ravi Malaviya、Cangming Yang、Rochelle Argentieri、Bingbing Wang、Xin Chen、William V. Murray、Druie Cavender

DOI：10.1016/j.bmcl.2009.04.039

日期：2009.6

The synthesis and biological evaluation of JAK3 based staurosporine compounds is described. The compounds are constructed completely de novo, and a ring closing metathesis strategy is used to assemble the sugar mimetic portion. These analogs show potent JAK3 activity against isolated enzyme and in T-cells. One analog (32) showed unique biological effects during in vitro and in vivo tests including

描述了基于JAK3的星形孢菌素化合物的合成和生物学评估。这些化合物完全从头构建，并且采用闭环复分解策略组装糖模拟部分。这些类似物显示出对分离的酶和T细胞有效的JAK3活性。一种类似物（32）在体外和体内试验中表现出独特的生物学作用，包括在过敏性疾病小鼠模型中抑制STAT5磷酸化，阻断肥大细胞反应以及降低基于JAK3的作用。
Substituted indolo[2,3-a]pyrrolo[3,4-c]carbazole compounds useful in treating kinase disorders

申请人：Wilson J. Lawrence

公开号：US20070249590A1

公开（公告）日：2007-10-25

The present invention is directed to substituted indolo[2,3-a]pyrrolo[3,4-c]carbazole compounds of formula (I): and forms thereof and their synthesis and use as protein kinase inhibitors and interactions thereof.

本发明涉及式(I)的取代吲哚[2,3-a]吡咯[3,4-c]咔唑化合物及其形式，以及它们的合成和用作蛋白激酶抑制剂及其相互作用的用途。