(1-amino-3-ammoniopropylidene)ammonium dihydrobromide | 119962-92-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1-amino-3-ammoniopropylidene)ammonium dihydrobromide
• 英文别名: β-aminopropionamidine dihydrobromide；3-aminopropionamidine dihydrobromide；3-Aminopropanimidamide--hydrogen bromide (1/1)；3-aminopropanimidamide;hydrobromide
• CAS: 119962-92-4
• 化学式: 2BrH*C₃H₉N₃
• 分子量: 248.948
• InChiKey: ZETQEMOLHGSXHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.9
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Succinimidyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate 、 (1-amino-3-ammoniopropylidene)ammonium dihydrobromide 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 司他霉素
  参考文献：
  名称：

  Synthesis and antiviral activity of distamycin A analogs: substitutions on the different pyrrole nitrogens and in the amidine function

  摘要：

  Several new analogues of the antiviral antibiotic distamycin A were synthesized and assayed for their effects on influenza and herpes simplex virus. The new compounds 5b-j (R1-3 = H, CH3, and C2H5, R4,5 = H and CH3) were obtained via stepwise prepared formylated trimeric benzyl 4-aminopyrrole-2-carboxylates 3a-h, which after catalytic hydrogenolysis were coupled as N-succinimidyl esters directly with the proper beta-aminopropionamidine, unsubstituted or substituted with one or two methyl groups in the amidine function. Most of the new analogues did not exhibit significant effects on the viruses studied, but three compounds (5f-h) displayed activity on herpes virus as demonstrated in plaque formation and virus yield assays. Elevated cytotoxicity was simultaneously observed for 5g and 5h. For compound 5f, a partial separation of antiherpes activity and cytotoxicity was accomplished. The differences in antiherpes activity did not correspond to the differences in the inhibition of herpes virus DNA polymerase.

  DOI：

  10.1021/jm00361a018
• 作为产物：
  描述：

  3-(p-toluenesulfonylamino)-propionamidine 在 氢溴酸 、 苯酚 作用下， 以 溶剂黄146 为溶剂， 生成 (1-amino-3-ammoniopropylidene)ammonium dihydrobromide
  参考文献：
  名称：

  含有噻唑氨基酸残基的抗肿瘤药双霉素的二肽类似物

  摘要：

  合成了三种与天然抗病毒抗肿瘤药奈特罗普星和双霉素有关的化合物。它们是从2-（（氨基甲基）-噻唑-4羧酸gly（Thz）（高细胞毒性天然肽结构中的关键元素）开始设计的，在这三种新化合物的结构中，该单元取代了N-甲基吡咯羧酸，似乎在母体天然物质识别DNA碱基序列中起关键作用。

  DOI：

  10.1016/s0040-4020(01)81440-x

文献信息

• Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition
  作者：Stephen G. Davies、Jane R. Haggitt、Osamu Ichihara、Richard J. Kelly、Michael A. Leech、Anne J. Price Mortimer、Paul M. Roberts、Andrew D. Smith

  DOI：10.1039/b404962d

  日期：——

  Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-alpha-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5-hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core

  将非手性锂（R）-N-烯丙基-N-α-甲基苄基酰胺的非对映选择性共轭加成到（2E，5E）-庚二烯酸甲酯中，然后进行保护基团处理，然后进行碘代环氨基甲酸酯化，可以得到通往核心片段甲基（3R，脂蛋白B和D的5R，6R）-3,6-二氨基-5-羟基庚酸酯。通过用丙酮处理，很容易实现该核心氨基酸的C-3和C-6伯氨基之间的区分。 ，6-异亚丙基和C-3-亚胺保护的二胺，随后C-6-氮的区域选择性酰化促进了总产率为10.8％的斯培比林D的总合成，以及首次总产率为5.8％的斯培比林B的不对称合成。 。
• Total asymmetric synthesis of sperabillins B and DElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b305740b/
  作者：Stephen G. Davies、Richard J. Kelly、Anne J. Price Mortimer

  DOI：10.1039/b305740b

  日期：——

  A consise route to the core fragment of sperabillins B and D, methyl (3R,5R,6R)-3,6-diamino-5-hydroxyheptanoate, has been developed with a subsequent novel protection strategy allowing the total asymmetric synthesis of sperabillins B and D.

  开发了一条简明的途径，直达海绵尿嘧啶B和D的核心片段，即甲基（3R,5R,6R）-3,6-二氨基-5-羟基庚酸酯，并随之采用了一种新颖的保护策略，实现了海绵尿嘧啶B和D的全不对称合成。
• Novel benzoyl nitrogen mustard derivatives of pyrazole analogues of distamycin A: synthesis and antileukemic activity
  作者：Pier Giovanni Baraldi、Paolo Cozzi、Cristina Geroni、Nicola Mongelli、Romeo Romagnoli、Giampiero Spalluto

  DOI：10.1016/s0968-0896(98)00205-3

  日期：1999.2

  The design and synthesis of novel benzoic acid mustard (BAM) derivatives of distamycin A bearing one or more pyrazole rings replacing the pyrrole rings of the latter are described. In vitro and in vivo activities against L1210 leukemia are reported and discussed. Some of these compounds show an activity profile comparable to tallimustine 1. All the compounds bearing the pyrazole ring close to the BAM

  本文描述了新型双酚A的苯甲酸芥末（BAM）衍生物的设计和合成，该衍生物带有一个或多个吡唑环替代了后者的吡咯环。报道和讨论了针对L1210白血病的体外和体内活性。这些化合物中的一些表现出与塔莫司汀1相当的活性。与以BAM与吡咯相连的衍生物相比，所有带有靠近BAM部分的吡唑环的化合物均显示出降低的细胞毒性：发生时未观察到相同的作用在寡肽框架的idine末端。
• Synthesis and Antiviral Activity of Three Pyrazole Analogues of Distamycin A.
  作者：Lu Ding、Leif Grehn、Erik De Clercq、Graciela Andrei、Robert Snoeck、Jan Balzarini、Bengt Fransson、Ulf Ragnarsson、George W. Francis

  DOI：10.3891/acta.chem.scand.48-0498

  日期：——

  The synthesis of three new monopyrazole analogues of the antiviral compound distamycin A is reported. Suitably protected 4-amino-1-methylpyrrole-2-carboxylic acid and 3-amino-1-methylpyrazole-5-carboxylic acid derivatives were chosen as starting materials. The construction of the trimeric polyamide framework was accomplished by assembly of the monomeric precursors under condensing conditions by analogy with our previous methodology, although with significant improvements in some pivotal steps. After chromatographic purification and spectroscopic characterisation, the analogues were assayed for antiviral activity. Compounds 7a-c inhibited vaccinia virus at a concentration similar to or lower than distamycin A and the related antibiotic netropsin. Analogues 7b and 7c exhibited an antiviral effect comparable to those of distamycin A and netropsin against HSV-1 and HSV-2, whereas their antiviral activity against several other viruses including HIV-1 and HIV-2 was somewhat lower. The cellular toxicity of 7a-c toward different host cell types proved to be of similar magnitude or lower than those of distamycin A and netropsin.
• Grehn; Ragnarsson; Datema, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 2 B, p. 145 - 150
  作者：Grehn、Ragnarsson、Datema

  DOI：——

  日期：——