氯苯吩嗪环合物盐酸盐 | 90690-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 氯苯吩嗪环合物盐酸盐
• 英文名称: 2-(4-chloranilino)-3,5-dihydro-5-(4-chlorphenyl)-3-iminophenazine hydrochloride
• 英文别名: 2-p-chloroanilino-5-p-chlorophenyl-3,5-dihydro-3-iminophenazine hydrochloride；N,5-Bis(4-chlorophenyl)-3-imino-3,5-dihydrophenazin-2-amine hydrochloride；N,5-bis(4-chlorophenyl)-3-iminophenazin-2-amine;hydrochloride
• CAS: 90690-85-0
• 化学式: C₂₄H₁₆Cl₂N₄*ClH
• 分子量: 467.785
• InChiKey: XTGVRWXXDDXLML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯苯吩嗪环合物盐酸盐 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 53.0h， 生成 2-[4-[4-[2-[(Z)-[3-(4-chloroanilino)-10-(4-chlorophenyl)phenazin-2-ylidene]amino]ethyl]piperazin-1-yl]butyl]benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  抗结核药。第1部分：邻苯二甲酰亚胺基和萘二甲酰亚胺基连接的吩嗪的合成，作为新的原型抗结核药。

  摘要：

  描述了一系列邻苯二甲酰亚胺基和萘二甲酰亚胺基连接的吩嗪的制备和抗结核特性。这些新化合物中的某些抑制结核分枝杆菌ATCC 27294，鸟分枝杆菌ATCC 49601，胞内分枝杆菌ATCC 13950和某些临床分离株的生长。

  DOI：

  10.1016/j.bmcl.2005.01.085
• 作为产物：
  描述：

  对氯苯胺 在 盐酸 、 三氯化铁 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 氯苯吩嗪环合物盐酸盐
  参考文献：
  名称：

  抗结核药。第1部分：邻苯二甲酰亚胺基和萘二甲酰亚胺基连接的吩嗪的合成，作为新的原型抗结核药。

  摘要：

  描述了一系列邻苯二甲酰亚胺基和萘二甲酰亚胺基连接的吩嗪的制备和抗结核特性。这些新化合物中的某些抑制结核分枝杆菌ATCC 27294，鸟分枝杆菌ATCC 49601，胞内分枝杆菌ATCC 13950和某些临床分离株的生长。

  DOI：

  10.1016/j.bmcl.2005.01.085

文献信息

• 一种化学合成的原料药及其治疗结核病及耐药性结核病的用途
  申请人：余述南

  公开号：CN114507189A

  公开（公告）日：2022-05-17

  本发明公开一种化学合成的原料药的制备方法，特别是公开化学合成氯法齐明原料药的制备方法，该原料药用于制备治疗结核病及耐药性结核病的药物。
• Clofazimine analogs with antileishmanial and antiplasmodial activity
  作者：Anna Barteselli、Manolo Casagrande、Nicoletta Basilico、Silvia Parapini、Chiara M. Rusconi、Michele Tonelli、Vito Boido、Donatella Taramelli、Fabio Sparatore、Anna Sparatore

  DOI：10.1016/j.bmc.2014.11.028

  日期：2015.1

  A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC50 in submicromolar range, resulting in the best cases 1-2 orders of magnitude more potent than the parent compound clofazimine. (C) 2014 Elsevier Ltd. All rights reserved.
• Clofazimine analogs active against a clofazimine-resistant organism
  作者：John F. O'Sullivan、Michael L. Conalty、Norman E. Morrison

  DOI：10.1021/jm00398a013

  日期：1988.3

  Clofazimine analogues active against a strain of Mycobacterium smegmatis 607 made resistant to the antileprosy agent have been synthesized. Activity (i.e., less than or equal to 2 micrograms/mL causing complete inhibition of growth) requires that there be a basic nitrogen in the "rimino" side chain and that the spacer distance between this nitrogen and the imino nitrogen be at least three carbon atoms. The nitrogen may be primary, secondary, or tertiary and may be part of an open chain or enclosed in a ring compound. Provided that the criteria of basicity and spacer distance are satisfied, all are active in vitro against both the sensitive and resistant strains. Substitution elsewhere in the molecule had little effect on the activity. The compounds have been shown to have growth inhibitory activity against human-derived Mycobacterium leprae in murine macrophages in culture.
• Antitubercular activity of quinolizidinyl/pyrrolizidinylalkyliminophenazines
  作者：Michele Tonelli、Federica Novelli、Bruno Tasso、Anna Sparatore、Vito Boido、Fabio Sparatore、Sara Cannas、Paola Molicotti、Stefania Zanetti、Silvia Parapini、Roberta Loddo

  DOI：10.1016/j.bmc.2014.10.035

  日期：2014.12

  Novel riminophenazine derivatives, characterized by the presence of the basic and cumbersome quinolizidinylalkyl and pyrrolizidinylethyl moieties, have been synthesized and tested (Rema test) against Mycobacterium tuberculosis H37Rv and H37Ra, and six clinical isolates of Mycobacterium avium and Mycobacterium tuberculosis. Most compounds exhibited potent activity against the tested strains, resulting more active than clofazimine, isoniazid and ethambutol.The best compounds (4, 5, 12 and 13) exhibited a MIC in the range 0.82-0.86 mu M against all strains of Mycobacterium tuberculosis and, with the exception of 4 a MIC around 3.3 mu M versus M. avium. The corresponding values for clofazimine (CFM) were 1.06 and 4.23 mu M, respectively. Cytotoxicity was evaluated against three cell lines and compound 4 displayed a selectivity index (SI) versus the human cell line MT-4 comparable with that of CFM (SI = 5.23 vs 6.4). Toxicity against mammalian Vero 76 cell line was quite lower with SI = 79. (C) 2014 Elsevier Ltd. All rights reserved.
• OSULLIVAN, J. F., J. CHEM. RES. SYNOP., 1984, N 2, 52-53
  作者：OSULLIVAN, J. F.

  DOI：——

  日期：——