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3-(1-methyl-4-(1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)dimethylaminopropane | 78486-18-7

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

——

中文别名

——

英文名称

3-(1-methyl-4-(1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)dimethylaminopropane

英文别名

3-<1-methyl-4-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamido>propyldimethylamine；aminodistamycin；aminolexitropsin；4-amino-N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide

3-(1-methyl-4-(1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)dimethylaminopropane化学式

CAS

78486-18-7

化学式

C₂₃H₃₂N₈O₃

mdl

——

分子量

468.559

InChiKey

KNCJHDJXRKMUQR-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

620.8±55.0 °C(Predicted)
密度：

1.30±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.2
重原子数：

34
可旋转键数：

9
环数：

3.0
sp3杂化的碳原子比例：

0.35
拓扑面积：

131
氢给体数：

4
氢受体数：

5

SDS

SDS：5a1a2abfb0f79e2434aedfcfcf9cdf52

查看

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
——	4-{[(4-amino-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1-methyl-1H-pyrrole-2-carboxamide	78486-16-5	C₁₇H₂₆N₆O₂	346.432
——	(5-{5-[5-(3-Dimethylamino-propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester	292069-89-7	C₂₈H₄₀N₈O₅	568.676
——	nitrolexitropsin	65361-32-2	C₂₃H₃₀N₈O₅	498.542
——	N-[3-(dimethylamino)propyl]-1-methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxamide	65361-31-1	C₁₇H₂₄N₆O₄	376.415
——	methyl 1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)-pyrrole-2-carboxylate	126092-99-7	C₁₃H₁₆N₄O₃	276.295
——	4-({4-[(4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carbonyl)amino]-1-methyl-1H-pyrrole-2-carbonyl}amino)-1-methyl-1H-pyrrole-2-carboxylic acid	126093-01-4	C₂₃H₂₈N₆O₆	484.512
——	3-(1-methyl-4-aminopyrrole-2-carbonylamino)propyldimethylamine	78486-14-3	C₁₁H₂₀N₄O	224.306
——	1-methyl-4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxylic acid	67974-03-2	C₁₈H₁₈N₆O₆	414.378
——	methyl 4-<<<4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate	126093-00-3	C₂₄H₃₀N₆O₆	498.539
——	methyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate	126092-97-5	C₁₈H₂₄N₄O₅	376.412
——	N-[3-(dimethylamino)propyl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide	65361-30-0	C₁₁H₁₈N₄O₃	254.289

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	Distamin	65361-29-7	C₂₄H₃₂N₈O₄	496.569
——	SL 11055	263020-08-2	C₂₉H₃₇N₉O₄	575.671
——	4-[[[4-[[[4-[[4-(hydroxyaminocarbonyl)valeryl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	——	C₂₉H₄₁N₉O₆	611.701
——	N-[5-({[5-({[3-(dimethylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(ethanimidoylamino)-1-methyl-1H-pyrrole-2-carboxamide	1000276-90-3	C₂₅H₃₅N₉O₃	509.611
——	4-[[[4-[[[4-[[4-(methoxycarbonyl)butyryl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	282088-90-8	C₂₉H₄₀N₈O₆	596.687
——	4-[[[4-[[[4-[[7-(methoxycarbonyl)heptanoyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	1027664-70-5	C₃₂H₄₆N₈O₆	638.767
——	N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methyl-pyrrol-3-yl]carbamoyl]-1-methyl-pyrrol-3-yl]-1-methyl-4-[[(E)-3-phenylprop-2-enoyl]amino]pyrrole-2-carboxamide	——	C₃₂H₃₈N₈O₄	598.705
——	4-[[[4-[[[4-[[5-(ethoxycarbonyl)valeryl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	282088-91-9	C₃₁H₄₄N₈O₆	624.74
——	3-[1-methyl-4-(1-methyl-4-(1-methyl-4-{1-methyl-4-nitropyrrole-2-carboxamido}pyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido]dimethylaminopropane	107580-24-5	C₂₉H₃₆N₁₀O₆	620.668
——	N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methyl-pyrrol-3-yl]carbamoyl]-1-methyl-pyrrol-3-yl]-4-[(3-methoxybenzoyl)amino]-1-methyl-pyrrole-2-carboxamide	——	C₃₁H₃₈N₈O₅	602.693
——	4-[[[4-[[[4-[[p-(methoxycarbonyl)phenylenecarbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	282088-96-4	C₃₄H₄₂N₈O₆	658.757
——	4-[[[4-[[[4-[[m-(methoxycarbonyl)phenylenecarbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	282088-95-3	C₃₄H₄₂N₈O₆	658.757
——	3-{1-methyl-4-[1-methyl-4-[1-methyl-4-(3-(4'-bromobenzoyl)propanoylamino)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido}dimethylaminopropane	——	C₃₃H₃₉BrN₈O₅	707.627
N-[5-({[5-({[3-(二甲氨基)丙基]氨基}羰基)-1-甲基-1H-吡咯-3-基]氨基}羰基)-1-甲基-1H-吡咯-3-基]-4-{[亚氨基(苯基)甲基]氨基}-1-甲基-1H-吡咯-2-甲酰胺	N-[5-({[5-({[3-(dimethylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-{[imino(phenyl)methyl]amino}-1-methyl-1H-pyrrole-2-carboxamide	1000276-88-9	C₃₀H₃₇N₉O₃	571.682
——	N-[5-({[3-(dimethylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-{[(4-{[imino(3-isoquinolinyl)methyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxamide	1000277-04-2	C₃₃H₃₈N₁₀O₃	622.73
——	4-[[[4-[[[4-[[o-(methoxycarbonyl)phenylenecarbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-2-pyrrolyl]carbonyl]amino]-1-methyl-N-[3-(N,N-dimethylamino)propyl]-2-pyrrolecarboxamide	282088-94-2	C₃₄H₄₂N₈O₆	658.757
——	N-{1-methyl-2-[1-methyl-2-(1-methyl-2-carboxamido(3-dimethylaminopropyl)-4-pyrrole)-carboxamido-4-pyrrole]carboxamido-4-pyrrolyl}-3-carboxypyridine-2-carboxamide	4939-06-4	C₃₀H₃₅N₉O₆	617.665
——	N-[3-(dimethylamino)propyl]-4-{[(4-{[(4-{[imino(3-methoxyphenyl)methyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxamide	1000276-89-0	C₃₁H₃₉N₉O₄	601.709
——	N-{1-methyl-2-[1-methyl-2-(1-methyl-2-carboxamido(3-dimethylaminopropyl)-4-pyrrole)-carboxamido-4-pyrrole]carboxamido-4-pyrrolyl}-phthalimide	——	C₃₁H₃₄N₈O₅	598.662
——	4-[4-[2,3-bis(hydroxymethyl)pyrrol-1-yl]butanoylamino]-N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methyl-pyrrol-3-yl]carbamoyl]-1-methyl-pyrrol-3-yl]-1-methyl-pyrrole-2-carboxamide	161677-86-7	C₃₃H₄₅N₉O₆	663.777
——	4-N-[2-[[2-[[2-[3-(dimethylamino)propylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-1-N-[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]benzene-1,4-dicarboxamide	——	C₅₁H₆₃N₁₉O₈	1070.18
——	(E)-N'-[2-[[2-[[2-[3-(dimethylamino)propylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-N-[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]but-2-enediimidic acid	——	C₄₇H₆₁N₁₉O₈	1020.12
——	4-N,11-N-bis[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-5,12-dimethyl-1,5,8,12-tetrazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarboxamide	——	C₆₁H₇₆N₂₀O₈	1217.4
——	4-[4-[4-[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]butanoylamino]-N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide	219931-73-4	C₄₄H₆₀N₁₀O₉S₂	937.154

反应信息

作为反应物：

描述：

3-(1-methyl-4-(1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)dimethylaminopropane 在 palladium on activated charcoal 4-二甲氨基吡啶、氢气、 N,N'-二环己基碳二亚胺作用下，以甲醇、 N,N-二甲基甲酰胺为溶剂， 20.0 ℃ 、413.68 kPa 条件下，反应 34.0h，生成

参考文献：

名称：

Lee, Moses; Simpson Jr., Jacob E.; Burns, Medicinal Chemistry Research, 1996, vol. 6, # 6, p. 365 - 371

摘要：

DOI：
作为产物：

描述：

1-甲基-4-硝基吡咯-2-羧酸在 palladium on activated charcoal 氯化亚砜、氢气、 1-羟基苯并三唑、 N,N'-二环己基碳二亚胺作用下，以 N,N-二甲基甲酰胺为溶剂，反应 29.0h，生成 3-(1-methyl-4-(1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)dimethylaminopropane

参考文献：

名称：

DNA亲和力裂解：Distamycin-EDTA-Fe（II）和EDTA-distamycin Fe（II）对DNA的序列特异性裂解

摘要：

的附接EDTA ·的Fe（II）到偏端霉素改变序列特异性DNA结合的抗生素为序列特异性DNA切割分子。我们报道了具有金属螯合剂EDTA的EDTA -distamycin（ED）的合成，该金属螯合剂被束缚在抗菌素distamycin的N-甲基吡咯三肽部分的羧基末端。EDTA -distamycin-的Fe（II）（ED）· FeII在10 -6 M个浓度有效地切割的pBR322 DNA（10 -5 M在碱基对）在氧和二硫苏糖醇的存在下（DTT）。使用Maxam-Gilbert测序凝胶分析，我们发现ED ·Fe（II）提供了不等强度的DNA裂解模式，覆盖了由腺嘌呤（A）和胸腺嘧啶（T）组成的5个碱基对位点附近的2至4个连续碱基对。每个位点的多次裂解可能是一种可扩散的氧化物质（可能是羟基）的证据。在A + T位点的每一侧的不均等的切割强度允许指定三肽结合单位的主要和次要方向。ED ·Fe（II）与双歧霉素-EDTA

DOI：

10.1016/0040-4020(84)85050-4

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文献信息

[EN] CONJUGATES FOR TREATING DISEASES<br/>[FR] CONJUGUÉS POUR LE TRAITEMENT DE MALADIES

申请人：ENDOCYTE INC

公开号：WO2016148674A1

公开（公告）日：2016-09-22

The present disclosure relates to pyrrolobenzodiazepine (PBD) prodrugs and conjugates thereof. The present disclosure also relates to pharmaceutical compositions of the conjugates described herein, methods of making and methods of using the same.

本公开涉及吡咯苯并二氮杂环（PBD）前药及其结合物。本公开还涉及所述结合物的药物组合物，制备方法和使用方法。
Antimicrobial Lexitropsins Containing Amide, Amidine, and Alkene Linking Groups

作者：Nahoum G. Anthony、David Breen、Joanna Clarke、Gavin Donoghue、Allan J. Drummond、Elizabeth M. Ellis、Curtis G. Gemmell、Jean-Jacques Helesbeux、Iain S. Hunter、Abedawn I. Khalaf、Simon P. Mackay、John A. Parkinson、Colin J. Suckling、Roger D. Waigh

DOI：10.1021/jm070831g

日期：2007.11.1

-resistant strains, in the range of 0.1-5 microg mL-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 microg mL-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. aureus infection for a period of up to six days after a single

描述了80种与二霉素和噻唑类相关的短小沟结合剂的合成和性能。化合物的设计主要基于小沟结合剂和DNA之间的疏水相互作用而增加的亲和力。疏水性芳族头基（包括喹啉基和苯甲酰基衍生物）的引入以及烯烃作为连接剂的引入，导致几种具有MIC的金黄色葡萄球菌的强活性抗菌化合物（对甲氧西林敏感和耐药的菌株）范围为0.1-5 microg mL -1，与许多已建立的抗菌剂相当。还发现针对黑曲霉和白色念珠菌的抗真菌活性为20-50微克mL-1 MIC，再次与已确立的抗真菌药物相当。
Synthesis of Geometrically Constrained Unsymmetrical Bis(polyamides) Related to the Antiviral Distamycin

作者：Sanjay K. Sharma、Manju Tandon、J. William Lown

DOI：10.1002/1099-0690(200006)2000:11<2095::aid-ejoc2095>3.0.co;2-j

日期：2000.6

for the strict DNA base-sequence recognition of (AT)4 and (AT)5, respectively, for the oligopeptide minor-groove binding agents netropsin (I) and distamycin (II) leads to proposals for the rational structure modification for altered base recognition. In this paper we report the synthesis of unsymmetrical imidazo-pyrrolo-bis(polyamides), structurally related to the natural antiviral agents distamycin

分析分别对（AT）4和（AT）5的寡肽小沟结合剂netropsin（I）和distamycin（II）的严格DNA碱基序列识别的结构和立体化学要求导致了对合理的结构修饰，以改变碱基识别。在本文中，我们报告了与天然抗病毒剂双歧霉素在结构上相关且带有非天然（25-27）或天然（31-33）的不对称咪唑并吡咯并双（聚酰胺）的合成）由柔性或刚性接头链接的末端。这是关于在连接的双（聚酰胺）中具有二甲基氨基丙基或am基末端的带有咪唑的结构的合成的首次报道。
Distamycin Analogues with Enhanced Lipophilicity: Synthesis and Antimicrobial Activity

作者：Abedawn I. Khalaf、Roger D. Waigh、Allan J. Drummond、Breffni Pringle、Ian McGroarty、Graham G. Skellern、Colin J. Suckling

DOI：10.1021/jm031089x

日期：2004.4.1

Forty-eight heterocyclic amino acid trimers, analogues of distamycin, with a number of features that enhance lipophilicity are described. They contain alkyl or cycloalkyl groups larger than methyl; some are N-terminated by acetamide or methoxybenzamide and are C-terminated by dimethylaminopropyl or aliphatic heterocylic aminopropyl substituents. The ability of these compounds to bind principally to

描述了四十八个杂环氨基酸三聚体，它是二霉素的类似物，具有许多增强亲脂性的特征。它们含有比甲基大的烷基或环烷基；一些被乙酰胺或甲氧基苯甲酰胺N端基，并且被二甲氨基丙基或脂族杂环甲基氨基丙基取代基C端基。使用毛细管区带电泳已经评估了这些化合物主要结合至DNA AT束的能力。几种化合物，特别是那些含有噻唑的化合物，显示出对关键生物如MRSA和白色念珠菌的显着抗菌活性。而且，这些化合物对几种哺乳动物细胞系具有低毒性。
Artemisinin-Polypyrrole Conjugates: Synthesis, DNA Binding Studies and Preliminary Antiproliferative Evaluation

作者：Louise La Pensée、Sunil Sabbani、Raman Sharma、Inder Bhamra、Emma Shore、Amy E. Chadwick、Neil G. Berry、James Firman、Nuna C. Araujo、Lília Cabral、Maria L. S. Cristiano、Cerys Bateman、Omar Janneh、Adelina Gavrila、Yi Hang Wu、Afthab Hussain、Stephen A. Ward、Paul A. Stocks、Rick Cosstick、Paul M. O'Neill

DOI：10.1002/cmdc.201200536

日期：2013.5

trials against breast, colorectal and non‐small‐cell lung cancers. In an attempt to offer increased specificity, a series of hybrid artemisinin–polypyrrole minor groove binder conjugates are described. DNA binding/modelling studies and preliminary biological evaluation give insights into their mechanism of action and the potential of this strategy.

大于其各部分的总和：青蒿素目前正处于针对乳腺癌、结直肠癌和非小细胞肺癌的 I-II 期临床试验中。为了提供更高的特异性，描述了一系列混合青蒿素-聚吡咯小沟结合剂偶联物。DNA 结合/建模研究和初步生物学评估可以深入了解其作用机制和该策略的潜力。