3,4-二氨基苯甲酸甲酯盐酸盐 | 1210824-92-2

• 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: 3,4-二氨基苯甲酸甲酯盐酸盐
• 英文名称: methyl 3,4-diaminobenzoate dihydrochloride
• 英文别名: 3,4-diaminobenzoic acid methyl ester dihydrochloride；3,4-Diaminobenzoic Acid Methyl Ester Hydrochloride；methyl 3,4-diaminobenzoate;hydrochloride
• CAS: 1210824-92-2
• 化学式: C₈H₁₀N₂O₂*2ClH
• 分子量: 239.101
• InChiKey: VHQRLZRJSQHZSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二氨基苯甲酸甲酯盐酸盐 在 吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 methyl 3-[(4-tert-butylbenzoyl)amino]-4-[(4-methoxybenzoyl)amino]benzoate
  参考文献：
  名称：

  1,2-Dibenzamidobenzene Inhibitors of Human Factor Xa

  摘要：

  High-throughput screening of a combinatorial library of diamidophenols yielded lead compounds with the ability to inhibit human factor Xa (fXa) at micromolar concentrations (e.g. compound 4, fXa apparent K-ass = 0.64 x 10(6) L/mol). SAR studies in this novel structural series of fXa inhibitors showed that the phenolic hydroxyl group was not essential for activity. The best activity was found in substituted 1,2-dibenzamidobenzenes in which the phenyl group of one benzoyl group (A-ring) was substituted in the 4-position with relatively small lipophilic or polarizable groups such as methoxy, vinyl, or chloro and the phenyl group of the other benzoyl group (B-ring) was substituted in the 4-position with larger lipophilic groups such as tert-butyl or dimethylamino. The central phenyl ring (C-ring) tolerated a wide variety of substituents, but methoxy, methanesulfonamido, hydroxyl, and carboxyl substitution produced slightly higher levels of activity than other substituents when present in combination with favorable B-ring substitution. Methylation of the amide nitrogen atoms was found to greatly decrease activity. Compound 12 is the highest affinity fXa inhibitor in this group of compounds, having fXa apparent K-ass = 25.5 x 10(6) L/mol, about 40x more active than the original lead. This lead series does not show potent inhibition of human thrombin. A model for the binding of these ligands to the fXa active site is proposed. The model is consistent with the observed SAR and can serve to guide future SAR studies.

  DOI：

  10.1021/jm990326m
• 作为产物：
  描述：

  3,4-二硝基苯甲酸甲酯 在 palladium on activated charcoal 三乙基硅烷 、 氯仿 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以100%的产率得到3,4-二氨基苯甲酸甲酯盐酸盐
  参考文献：
  名称：

  Pd−C-Induced Catalytic Transfer Hydrogenation with Triethylsilane

  摘要：

  In situ generation of molecular hydrogen by addition of triethylsilane to palladium-charcoal catalyst results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection under mild, neutral conditions.

  DOI：

  10.1021/jo0706123

文献信息

• Benzimidazole, Benzoxazole and Benzothiazole Derivatives, Optical Film Comprising them and Method of Producing thereof
  申请人：Nokel Alexey

  公开号：US20100279122A1

  公开（公告）日：2010-11-04

  The present invention is relates to the synthesis of predominantly planar heterocyclic organic compound and the manufacture of optical films based on these compounds. Said organic compound has the general structural formula where Het is a predominantly planar heterocyclic molecular system possessing hydrophilic properties; B is a binding group; p is the number in the range from 3 to 8; S is a group providing solubility of the organic compound; m is a number in the range from 0 to 8. Said organic compound is transparent for electromagnetic radiation in the visible spectral range from 400 to 700 nm, and a solution of the compound or a salt thereof is capable of forming a substantially transparent optical layer on a substrate, with the heterocyclic molecular planes oriented predominantly parallel to the substrate surface.

  本发明涉及主要呈平面状的杂环有机化合物的合成以及基于这些化合物的光学薄膜的制造。所述有机化合物具有通用结构公式，其中Het是一个主要呈平面状的具有亲水性质的杂环分子体系；B是一个结合基团；p是一个3到8之间的数；S是一个提供有机化合物溶解度的基团；m是一个0到8之间的数。所述有机化合物对可见光谱范围内400到700纳米的电磁辐射是透明的，并且该化合物或其盐的溶液能够在基底上形成基本透明的光学层，其中杂环分子平面主要平行于基底表面。
• Antithrombotic agents
  申请人：Eli Lilly and Company

  公开号：US06313122B1

  公开（公告）日：2001-11-06

  This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  这项申请涉及到式(I)的化合物，该化合物的药用盐或其前药，如本文所定义，以及其药物组合物，以及其作为Xa因子抑制剂的用途，以及其制备方法和中间体。
• EP1505067
  申请人：——

  公开号：——

  公开（公告）日：——
• Anticancer Activity of Hydrogen-Bond-Stabilized Half-Sandwich Ru^IIComplexes with Heterocycles
  作者：Raja Mitra、Sangeeta Das、Sridevi V. Shinde、Sarika Sinha、Kumaravel Somasundaram、Ashoka G. Samuelson

  DOI：10.1002/chem.201200938

  日期：2012.9.24

  AbstractNeutral half‐sandwich organometallic ruthenium(II) complexes of the type [(η6‐cymene)RuCl2(L)] (H1–H10), where L represents a heterocyclic ligand, have been synthesized and characterized spectroscopically. The structures of five complexes were also established by single‐crystal X‐ray diffraction confirming a piano‐stool geometry with η6 coordination of the arene ligand. Hydrogen bonding between the NH group of the heterocycle and a chlorine atom attached to Ru stabilizes the metal–ligand interaction. Complexes coordinated to a mercaptobenzothiazole framework (H1) or mercaptobenzoxazole (H6) showed high cytotoxicity against several cancer cells but not against normal cells. In vitro studies have shown that the inhibition of cancer cell growth involves primarily G1‐phase arrest as well as the generation of reactive oxygen species (ROS). The complexes are found to bind DNA in a non‐intercalative fashion and cause unwinding of plasmid DNA in a cell‐free medium. Surprisingly, the cytotoxic complexes H1 and H6 differ in their interaction with DNA, as observed by biophysical studies, they either cause a biphasic melting of the DNA or the inhibition of topoisomerase IIα activity, respectively. Substitution of the aromatic ring of the heterocycle or adding a second hydrogen‐bond donor on the heterocycle reduces the cytotoxicity.
• US6313122B1
  申请人：——

  公开号：US6313122B1

  公开（公告）日：2001-11-06