1-(3,4-二氯苯基)双胍 盐酸盐 | 21703-08-2

• 物质功能分类: 化学试剂 - 有机试剂 - 胍盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3,4-二氯苯基)双胍 盐酸盐
• 中文别名: 1-(3,4-二氯苯基)双胍盐酸盐；1-(3,4-二氯苯基)缩二胍盐酸盐
• 英文名称: N5-3,4-(dichloro)phenyl biguanide hydrochloride
• 英文别名: 3,4-Dichlorophenylbiguanide hydrochloride；[N'-[N'-(3,4-dichlorophenyl)carbamimidoyl]carbamimidoyl]azanium;chloride
• CAS: 21703-08-2
• 化学式: C₈H₉Cl₂N₅*ClH
• 分子量: 282.56
• InChiKey: AMMSXYWPWHREDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  222-228 °C(lit.)
• 稳定性/保质期：
  按规定使用和贮存的不会分解，应避免接触氧化物和潮湿环境。

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  1-(3,4-二氯苯基)双胍 盐酸盐 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 67.0h， 生成 1-(3,4-Dichlorophenyl)-2-[4-[3-(ethylaminomethyl)-4-hydroxyanilino]-6-(trifluoromethyl)pyrimidin-2-yl]guanidine
  参考文献：
  名称：

  Synthesis and antifilarial activity of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]-2-pyrimidinyl]-N'-phenylguanidines

  摘要：

  A series of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]- 2-pyrimidinyl]-N'-phenylguanidines have been synthesized for antifilarial evaluation. Reaction of the appropriate benzenamines with N-cyanoguanidine, followed by condensation of the resultant N-phenylimidodicarbonimidic diamides (V) with ethyl 4,4,4-trifluoro-3-oxobutanoate provided the intermediate N-(4-hydroxy-2-pyrimidinyl)-N'-phenylguanidines VIa. Alternatively, compounds VIa were synthesized by reaction of the requisite beta-keto esters (VII) with N-cyanoguanidine to give the (4-hydroxy-2-pyrimidinyl)cyanamides (VIII), followed by treatment with the desired benzenamines. Chlorination with POCl3 and condensation with the appropriate benzenamines (IX) generated the desired guanidines (X). Antifilarial activity was confined to adult Litomosoides carinii infections, and a structure-activity relationship for this activity is discussed. Lack of activity against L. carinii microfilaria and adult Brugia pahangi infections preclude further work in this area pending evaluation in additional experimental models.

  DOI：

  10.1021/jm00363a010
• 作为产物：
  描述：

  3,4-二氯苯胺 、 二聚氰胺 在 盐酸 作用下， 以 水 为溶剂， 反应 0.17h， 生成 1-(3,4-二氯苯基)双胍 盐酸盐
  参考文献：
  名称：

  Structural Insights into the Development of Cycloguanil Derivatives asTrypanosoma bruceiPteridine-Reductase-1 Inhibitors

  摘要：

  Cycloguanil is a known dihydrofolate-reductase (DHFR) inhibitor, but there is no evidence of its activity on pteridine reductase (PTR), the main metabolic bypass to DHFR inhibition in trypanosomatid parasites. Here, we provide experimental evidence of cycloguanil as an inhibitor of Trypanosoma brucei PTR1 (TbPTR1). A small library of cycloguanil derivatives was developed, resulting in 1 and 2a having IC50 values of 692 and 186 nM, respectively, toward TbPTR1. Structural analysis revealed that the increased potency of 1 and 2a is due to the combined contributions of hydrophobic interactions, H-bonds, and halogen bonds. Moreover, in vitro cell-growth-inhibition tests indicated that 2a is also effective on T. brucei. The simultaneous inhibition of DHFR and PTR1 activity in T. brucei is a promising new strategy for the treatment of human African trypanosomiasis. For this purpose, 1,6-dihydrotriazines represent new molecular tools to develop potent dual PTR and DHFR inhibitors.

  DOI：

  10.1021/acsinfecdis.8b00358

文献信息

• AN EFFICIENT SYNTHESIS OF 1-ARYL-4,6-DIAMINO-1,2-DIHYDRO- 1,3,5-TRIAZINES
  作者：Neungruthai Saesaengseerung、Tirayut Vilaivan、Yodhathai Thebtaranonth

  DOI：10.1081/scc-120005415

  日期：2002.1.1

  ABSTRACT 1-Aryl-4,6-diamino-1,2-dihydro-1,3,5-triazines bearing diverse substituents at C2 and on the aromatic ring have been synthesized in good yield from an acid-catalyzed reaction between corresponding arylbiguanide and carbonyl compound in the presence of triethyl orthoacetate as a water scavenger.

  摘要 1-Aryl-4,6-diamino-1,2-dihydro-1,3,5-triazines 在 C2 和芳环上具有不同的取代基，通过相应的芳基双胍和芳环之间的酸催化反应合成，收率良好。在作为水清除剂的原乙酸三乙酯存在下羰基化合物。
• Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0507317A2

  公开（公告）日：1992-10-07

  The invention presents a biguanide derivative or its salt expressed by a formula: (where R1 and R2 are as defined in Specification), or formula: (where A and R3 is as defined in specification). This biguanide derivative or its salt is preferably used as the effective amount of a disinfectant for humans, animals, medical appliances, etc.

  本发明提出了一种由式表示的双胍衍生物或其盐： (其中 R1 和 R2 如说明书中所定义），或式 (式中A和R3的定义见说明书）。这种双胍衍生物或其盐最好用作人、动物、医疗器械等有效量的消毒剂。
• Synthesis of Solution-Phase Combinatorial Library of 4,6-Diamino-1,2-dihydro-1,3,5-triazine and Identification of New Leads Against A16V+S108T Mutant Dihydrofolate Reductase of Plasmodium falciparum
  作者：Tirayut Vilaivan、Neungruthai Saesaengseerung、Deanpen Jarprung、Sumalee Kamchonwongpaisan、Worachart Sirawaraporn、Yongyuth Yuthavong

  DOI：10.1016/s0968-0896(02)00344-9

  日期：2003.1

  An efficient method to synthesize solution-phase combinatorial library of 1-aryl-4,6-diamino-1,2-dihydro-1,3,5-triazine was developed. The strategy involved an acid-catalyzed cyclocondensation between arylbiguanide hydrochlorides and carbonyl compounds in the presence of triethyl orthoacetate as water scavenger. A 96-membered combinatorial library was constructed from 6 aryl biguanides and 16 carbonyl compounds. Screening of the library by iterative deconvolution method revealed two candidate leads which are equally active against wild-type Plasmodium falciparum dihydrofolate reductase, but are about 100-fold more effective against the A16V + S108T mutant enzyme as compared to cycloguanil. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US2803628
  申请人：——

  公开号：——

  公开（公告）日：——
• DE879696
  申请人：——

  公开号：——

  公开（公告）日：——